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Izzie Stevens
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Dr. Izzie Stevens
Grey's Anatomy character
The Season 6 Promotional Photo of Katherine Heigl as Dr. Izzie Stevens
First appearance
"A Hard Day's Night"
1x01, March 27, 2005
Last appearance
"I Like You So Much Better When You're Naked"
6x12, January 21, 2010
Created by
Shonda Rhimes
Portrayed by
Katherine Heigl
Information
Full name
Isobel Katherine Stevens
Nickname(s)
Dr. Model
Cricket
Izz
Izzie
Barbie
Tinkerbell
Stevens
Patient X
Bethany Whisper
Blondie
Cancer Wife
Title
M.D.
Family
Robbie Stevens (Mother)
Hannah Klein (Daughter)
Spouse(s)
Alex Karev (divorced)
Significant other(s)
Hank
Denny Duquette
(fiancé, deceased)
George O'Malley (deceased)
Religion
Catholicism
Isobel Katherine "Izzie" Stevens, M.D. is a fictional character from the medical drama television series Grey's Anatomy, which airs on the American Broadcasting Company (ABC) in the United States. The character was created by series producer Shonda Rhimes, and was portrayed by actress Katherine Heigl from 2005 to 2010. Introduced as a surgical intern at the fictional Seattle Grace Hospital, Izzie worked her way up to resident level, while her relationships with her colleagues Meredith Grey (Ellen Pompeo), Cristina Yang (Sandra Oh), George O'Malley (T.R. Knight) and Alex Karev (Justin Chambers) formed a focal point of the series.
Heigl garnered critical acclaim for her performance as Izzie and received numerous awards and nominations for her role, winning the "Outstanding Supporting Actress In A Drama Series" at the 2007 Emmy Awards. She was critical of the character's development during the show's fourth season, particularly her romance with George. She declined to put herself forward for the 2008 Emmy Awards, citing insufficient material in the role. After speculation that Izzie would be killed off in the fifth season, the character was diagnosed with Stage 4 metastatic melanoma. She married Alex in the series' one-hundredth episode, and afterwards, her tumor was successfully removed. Izzie made her final appearance in the sixth season, leaving Seattle after Alex refused to resume their marriage. Heigl requested to be released from her contract 18 months early, in order to spend more time with her family. In January 2012, Heigl reported that she would like to return to Grey's Anatomy to give closure to her character, however, Rhimes confirmed that there were no plans to have the character return at that time and has since stated that she has no plans to ever re-approach Izzie's storyline again.
Contents
[hide]
1 Storylines
2 Development
2.1 Casting and creation
2.2 Characterization
3 Reception
4 References
5 External links
Storylines[edit]
Izzie appears in the first episode of Grey's Anatomy, meeting fellow interns Meredith Grey, Cristina Yang, Alex Karev, and George O'Malley.[1] She and George move in with Meredith and become best friends.[2] Izzie's boyfriend, hockey player Hank (Jonathan Scarfe), struggles to accept her new role as a surgeon, and the two break up.[3] Izzie is hurt when Alex exposes her past as a lingerie model.[4] However, the two later go on to begin a friendship and then a romance.[5] Alex experiences sexual dysfunction with Izzie and cheats on her with nurse Olivia Harper (Sarah Utterback).[6] When Izzie finds out, she breaks up with him, though they briefly reunite following a bomb incident at the hospital.[7] Izzie reveals while treating a pregnant teenager that she had a daughter at the age of 16 and gave up for adoption. Izzie falls in love with cardiothoracic patient Denny Duquette (Jeffrey Dean Morgan), and the two become engaged. When Denny's condition deteriorates, Izzie deliberately worsens his health further by cutting his LVAD wire to move him up the donor register.[8] Although Denny receives a new heart, he has a stroke hours later and dies.[9] Izzie is the sole beneficiary of Denny's will, inheriting $8.7 million.[10] She uses the money to open a free clinic at the hospital: the Denny Duquette Memorial Clinic.[11]
Izzie disapproves of George's relationship and marriage to orthopedic resident Callie Torres (Sara Ramirez).[12] She and George sleep together, and attempt to keep their liaison a secret.[13] George and resident Miranda Bailey (Chandra Wilson) are the only people aware that Izzie gave birth to a daughter at the age of sixteen; ultimately the child was given up for adoption. He supports Izzie when her daughter Hannah (Liv Hutchings), diagnosed with leukemia, arrives at Seattle Grace Hospital in need of a bone marrow transplant from Izzie.[14] Izzie's feelings for George grow, and she reveals that she has fallen in love with him.[15] When Callie discovers George has been unfaithful, the two separate,[16] and George and Izzie embark on a short-lived relationship, only to discover there is no real chemistry between them.[17]
Izzie supports Alex when he discovers his new girlfriend has psychiatric problems, and convinces him to have her committed. She is also handed primary responsibility for the clinic, as Bailey cuts back on her responsibilities.[18] Izzie and Alex go on to rekindle their relationship, though Izzie is concerned when she begins hallucinating Denny.[19] She discovers she has metastatic melanoma (Stage IV) which has spread to her liver, skin, and brain, causing the hallucinations. Her survival chances are estimated at only 5%.[20] She is admitted to Seattle Grace as a patient, and Derek Shepherd (Patrick Dempsey) successfully removes a tumor from her brain.[21] Izzie spends her time in the hospital planning Meredith and Derek's wedding, but when her condition worsens and Derek discovers a second brain tumor, they give the ceremony to Izzie and Alex, who marry in front of all their friends.[22] The procedure to remove the second tumor from Izzie's brain causes her to lose her short-term memory, and although she soon regains it, she flatlines moments later. The fifth season ends with her friends ignoring her DNR order and attempting to resuscitate her, transposed with images of Izzie in an elevator encountering George, who has been in an accident and is also currently flatlining.[23] Though George dies, Izzie is resuscitated and recovers enough to return to work.[24]
Izzie makes a treatment error that endangers the life of a patient, and is fired from the hospital's surgical program. Believing Alex is partially to blame, she writes him a Dear John letter and leaves.[25] Izzie later learns that Alex was not responsible for her lost job, and returns to make amends with him, but Meredith informs her that Alex is moving on. Izzie informs Alex that she no longer has cancer. Although he is pleased, Alex officially breaks up with Izzie, telling her that he loves her but deserves better. She leaves Seattle to start fresh.[26] Several episodes later, Alex informs Meredith that Izzie sent divorce papers, which he signs in the episode "How Insensitive".[27] In the sixth-season finale, Alex is shot and asks for Izzie. Imagining that Meredith's half-sister Lexie (Chyler Leigh) is Izzie, he apologizes and asks her never to leave him again.[28]
Development[edit]
Casting and creation[edit]
Heigl refused to be considered for the 2008 Emmy Awards due to insufficient material on Grey's Anatomy.
Izzie was created by Grey's Anatomy producer Shonda Rhimes, with actress Katherine Heigl cast in the role. Heigl originally wanted to play Izzie as a brunette, but was requested to retain her natural blond for the part.[29] Heigl's comprehension of medical procedures and terminology is slight; the actress explained that while she has an admiration for doctors, she is not as fascinated by medicine as other cast members.[30] When Kate Walsh's character Addison Montgomery left Grey's Anatomy to launch the spin-off show Private Practice, Heigl disclosed that she had hoped for a spin-off for Izzie.[31]
Heigl declined to put her name forward for consideration at the 2008 Emmy Awards, claiming that she had been given insufficient material on the series to warrant a nomination.[32] Following Heigl's statement, speculation arose that her character would suffer a brain tumor and be killed off Grey's Anatomy, substantiated by the announcement Jeffrey Dean Morgan would return to the series as Denny, who died at the end of season two.[33] ABC's entertainment president Steve McPherson denied the rumor, stating: "There is an unbelievable storyline for her this year, which is really central to everything that's going to go on this season".[34]
Speculation resumed, however, when Dean Morgan returned to the show for a second time in its fifth season.[35] Cast member James Pickens, Jr. announced that both Heigl and T.R. Knight were set to depart from the show,[36] but he later retracted his comment.[37] During the course of the fifth season, Izzie was diagnosed with metastatic melanoma (Stage IV) which spread to her liver, skin and brain. Following the show's one-hundredth episode wrap party, Heigl revealed she did not know if Izzie would survive, as no one on the production team would disclose her character's fate to her.[38] It was confirmed in June 2009 that Heigl would return as Izzie for the show's sixth season.[39] Heigl's appearances in the season were sporadic, seeing Izzie depart and return twice.[40] Although she was scheduled to appear in the final five episodes of the season, Heigl requested that she be released from her contract 18 months early, and made her final appearance on January 21, 2010.[41] Heigl explained that she wanted to spend more time with her family, and did not think it would be respectful to Grey's Anatomy viewers to have Izzie return and depart yet again.[40] Michael Ausiello spoke further on Katherine Heigl's perspective on Izzie's departure. He said, "[Katherine] thinks her Jan. 21 farewell - while not originally intended to be her last episode - oddly works as a bookend to Izzie's story. "Even though there's a part of me that would like to go back and do the quick Izzie farewell, " she says, "I also think that my last scene - where Meredith says to Izzie, 'Don't go, we're your family,' and Izzie's response was, 'No you're not, you're just a bunch of people I worked with, and I can find that anywhere' - was kind of tragic and appropriate all at the same time. When I was playing the scene I was really trying to convey that, for Izzie, that was a lie that she had to tell herself to have the courage to have to move on."[42]
In August 2010, Rhimes stated that she did not feel Izzie's character arc—specifically her relationship with Alex—had fully concluded, and hoped to give proper closure to their relationship in the seventh season.[43] She later confirmed that she had intended to kill off Izzie off-screen, but opted against this a day later as she felt that it would destroy Alex, rather than give him closure. Instead, she concluded: "I'm open to seeing Izzie again. So if she [Katherine] were to come back, we would be thrilled to [wrap up her story]. But if she doesn't, we'll just move on."[44] Heigl also went on to say in October 2010 that the character returning to show looks bleak because, "that chapter is closed, and it's sad. And it's hard." She also felt that Izzie coming back to the show would, "just feel manipulative."[45]
However, in January 2012, Heigl stated in an interview that she has asked the producers if she could return to the show to give closure to Izzie's storyline: "I've told them I want to [return]," she said. "I really, really, really want to see where [Izzie] is. I just want to know what happened to her and where she went and what she's doing now. My idea is that she actually like figures it out, and finds some success and does really well in a different hospital. She was always floundering you know, and so she was always one step behind the eight ball and I want to see that girl take some power back."[46] She later went on to say that she regrets leaving the show, "Oh yeah, sometimes, yeah. You miss it. I miss my friends. It was a great work environment ... and it becomes a family. I spent six years together with these people every day ... you grow up together, in a way," and again commented on Izzie possibly returning to the show, "I always felt that if they wanted me to come back and sort of wrap up that storyline ... I want them to know that I'm down with it if they want me to, but I completely understand if it doesn't necessarily work ... They've got a lot of story lines going on there."[47] But in March 2012, Shonda Rhimes said that there are no plans at the moment for the character to return, "I think it was really nice to hear her appreciating the show. At the same time we are on a track we have been planning. The idea of changing that track is not something we are interested in right now."[48] Three years later, Rhimes said she has completely moved on from the idea of Izzie coming back, “I’m done with that story. I’ve turned that idea over in my mind a thousand times and thought about how it would go. And I don’t think so.”[49]
Characterization[edit]
Heigl believes that the Grey's Anatomy writers incorporate much of the actors' personalities into their roles, and that Izzie is a "super moral" version of herself.[50] Episode "Bring the Pain", which aired as the fifth episode of the second season, was originally intended to be the final episode of the first season. Rhimes explained that Izzie's character in this episode came "full circle" from her role in the pilot: "Izzie, so vulnerable and underestimated when we first meet her, is the girl who removes her heart from her sleeve in "Bring the Pain"."[51] Discussing Izzie's personality in a 2006 Cosmopolitan interview, Heigl assessed that she is "immensely kind" and patient.[29] When Denny died in the season two episode "Losing My Religion", Rhimes discussed the impact it had on Izzie, noting that Izzie is forced to abandon her idealism, which in turn leads to her letting go of medicine.[52] In the aftermath of Denny's death, Heigl came to believe that Izzie was not cut out to be a doctor.[50] Executive producer Betsy Beers explained, however, that Denny's death served to make Izzie more mature,[50] and Heigl affirmed that "At the beginning of the [third] season they were trying to show how lost Izzie was. She lost her optimism. She realizes now that life is difficult, but she still tries very hard to see the best in people."[50] In order to demonstrate Izzie's dislike of George's love-interest Callie, Rhimes penned a scene which she deemed one of her favorite moments on the show, in which Callie urinates in front of a stunned Izzie and Meredith. Rhimes assessed that: "I love that Mer and Izzie respond with all the trauma of having viewed a car crash [...] the point is Callie pees and Izzie tortures her a tiny bit about the hand washing and that made me overjoyed because that’s the kind of thing people do."[53]
Discussing Izzie's relationship with Alex in a 2006 Cosmopolitan interview, Heigl assessed that "Even when Alex was a complete dirtbag to her [Izzie], she forgave him and gave him another chance. And he really screwed her over. [...] To go for a guy like that is to say I want to be damaged.'"[29] Writer Stacy McKee deemed Izzie's moving on from Alex to patient Denny Duquette "karma", as Alex previously treated Izzie badly, yet as he begins to realize his true feelings, he is forced to watch her embark on a romance with "the undeniably handsome - and totally charming" Denny.[54] Series writer Blythe Robe commented on Izzie and Denny: "I love the way Izzie lights up when she's around him. I love their relationship because it's so pure and honest and completely game free."[55] Writer Elizabeth Klaviter noted at this time the way Izzie "seems to be sacrificing her reputation because of her feelings for Denny."[56] When Izzie deliberately worsened Denny's condition to move him up the transplant list, series writer Mark Wilding questioned the morality of the actions, asking: "is Izzie bad for doing it? Is she tremendously irresponsible? She cut the LVAD wire for love so does that make her action understandable?"[57]
Heigl was critical of Izzie's relationship with George (T.R. Knight), deeming it "a ratings ploy".[58]
Rhimes discussed costuming choices in the scene which saw the interns gather around Denny's deathbed, explaining: "Meredith and George and Cristina and Callie and Alex are all dressed, not for a prom, but for a funeral. Everyone in dark colors, everyone dressed somberly. As if they were in mourning. Only Izzie is in happy pink. Only Izzie looks like she didn’t know this was coming."[52] Following Denny's death, Heigl approached Rhimes to ask when her character would next have a romantic liaison. Rhimes explained that "Izzie doesn't sleep around".[50] Heigl expressed a desire for Izzie to reunite with Alex, explaining: "I believe on some level, there's a connection between Izzie and Alex. He can do honorable things even though he's cutting and sarcastic. I would like to ultimately see them together, if not this season, then next."[50]
Yahoo! Voices wrote that Stevens in the third season "has become more condescending and passive aggressive herself, more than anyone else."[59] Heigl was critical of her character's development in the show's fourth season, particularly her affair with George, which she deemed "a ratings ploy".[58] Heigl explained: "They really hurt somebody, and they didn't seem to be taking a lot of responsibility for it. I have a really hard time with that kind of thing. I'm maybe a little too black and white about it. I don't really know Izzie very well right now. She's changed a lot."[58] Attempting to rationalise Izzie's actions, Heigl later assessed that:
People who are so infallible, perfect and moral tend to be the first to slip and fall. But I would love to see how she deals with the consequences of what she's done, because what’s interesting is when people make decisions that shake their world, they suddenly have to go, 'Woo, I didn't know I was capable of this.' I'd like to see Izzie take some culpability.[60]
Reception[edit]
Heigl was nominated for the "Best Supporting Actress in a TV Series" award at the 2007 and 2008 Golden Globe Awards for her role as Izzie.[61] She was named "Favorite Female TV Star" at the 34th People's Choice Awards,[62] and awarded "Outstanding Supporting Actress In A Drama Series" at the 2007 Emmy Awards.[63] Prior to the ceremony, considering Heigl's chances of winning the Emmy, Variety's Stuart Levine assessed of her performance: "Heigl has little difficulty reaching Izzie's highest highs and lowest lows. Showrunner Shonda Rhimes puts a lot of pressure on Heigl to carry many intense storylines, and she's up to the challenge."[64] Levine also noted, however: "There are times when Izzie becomes completely irrational during crisis situations, which may bother some."[64] Fox News included Izzie in its list of "The Best TV Doctors For Surgeon General".[65] The character was listed in Wetpaint's "10 Hottest Female Doctors on TV" and in BuzzFeed's "16 Hottest Doctors On Television".[66][67]
Heigl at the 59th Primetime Emmy Awards where she won the Outstanding Supporting Actress in a Drama Series Award.
During the show's third season, the New York Post's Robert Rorke deemed Izzie to be "the heart and soul" of Grey's Anatomy. He deemed her the show's heroine, and wrote that: "Izzie is a welcome, calming presence, despite the devastation she experienced when she failed to save her patient and fiance Denny Duquette. [...] Besides the formidable Dr. Bailey (Chandra Wilson), Izzie seems to be the only adult intern at Seattle Grace; the character has achieved a depth lacking in her fellow interns."[50] Eyder Peralta of The Houston Chronicle was critical of Izzie's ethics in cutting Denny's LVAD wire, writing that she "should not be practising medicine" and stating: "That's the reason I don't watch Grey's Anatomy, anymore, because the super hot blond chick can make an earth-shattering, fatal decision and she doesn't get canned."[68]
The season four romance between Izzie and George proved unpopular with viewers, and resulted in a fan backlash among Alex and Izzie fans.[69] The return of Izzie's deceased fiancé Denny and the resumption of their romance during the show's fifth season also proved unpopular with fans,[70] and was deemed "the world's worst storyline" by Mary McNamara of the Los Angeles Times.[71] McNamara was also critical of the episode "Now or Never", which saw Izzie flatline following neurosurgery, opining that Izzie ought to die.[71] The episode in which Izzie married long-term love Alex received 15.3 million viewers, the largest television audience of the night.[72]
Izzie's cancer storyline received a mixed response from the medical community. Otis Brawley, chief medical officer at the American Cancer Society, commented that Izzie's treatment options were unrealistic. Whereas in the show she was offered the drug interleukin-2, in reality the drug is never recommended to patients when melanoma has spread to the brain, as it can cause bleeding and strokes. Brawley explained that such patients would instead be offered radiosurgery.[73] Conversely however, Tim Turnham, executive director of the Melanoma Research Foundation, praised Grey's Anatomy for bringing about greater public awareness of melanoma, stating: "We welcome the national spotlight Grey's Anatomy has created for melanoma and its efforts to encourage viewers to learn more about the importance of prevention, early detection and research."[74]
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Jump up ^ "People's Choice Awards sidestep strike". USA Today. Gannett Company. January 9, 2008. Retrieved May 9, 2009.
Jump up ^ Lehner, Marla (September 18, 2007). "Katherine Heigl: Nobody Thought I'd Win the Emmy". People. Time Inc. Retrieved May 9, 2009.
^ Jump up to: a b Levine, Stuart (August 13, 2007). "Supporting Actress: Drama - Shades of 'Grey' for ABC's hospital gal pals". Variety. Reed Elsevier. Retrieved May 9, 2009.
Jump up ^ "The Best TV Doctors For Surgeon General". Fox News. Retrieved January 24, 2013.
Jump up ^ Martin, Rebecca (December 31, 2012). "The 10 Hottest Female Doctors on TV". Wetpaint. The Cambio Network. Retrieved January 25, 2013.
Jump up ^ "The 16 Hottest Doctors On Television". BuzzFeed. September 28, 2012. Retrieved January 25, 2013.
Jump up ^ Peralta, Eyder (February 16, 2007). "Tsk. Tsk. Ethics these days.". Houston Chronicle. Hearst Corporation. Retrieved July 21, 2009.
Jump up ^ Hughes, Sarah (November 17, 2008). "The power of Heroes worship". The Guardian. Guardian Media Group. Retrieved May 9, 2009.
Jump up ^ Collins, Scott (February 10, 2009). "Katherine Heigl & T.R. Knight: Are they really set to exit 'Grey's Anatomy?'". Los Angeles Times. Eddy Hartenstein. Retrieved July 21, 2009.
^ Jump up to: a b McNamara, Mary (May 15, 2009). "Dead or alive on 'Grey's Anatomy'?". Los Angeles Times. Eddy Hartenstein. Retrieved September 5, 2011.
Jump up ^ Toff, Benjamin; Itzkoff, David (May 8, 2009). "ABC's Wedding Gift". The New York Times. The New York Times Company. Retrieved May 9, 2009.
Jump up ^ Szabo, Liz (May 18, 2009). "Doctors, patients say 'Grey's' cancer story isn't accurate". USA Today. Gannett Company. Retrieved July 21, 2009.
Jump up ^ O'Brien, Ben (May 26, 2009). "'Grey's Anatomy' and melanoma". USA Today. Gannett Company. Retrieved July 21, 2009.
General
"Grey's Anatomy: Episode Recap Guide". ABC. Retrieved June 19, 2012.
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Diazonium compound
From Wikipedia, the free encyclopedia
Jump to navigation Jump to search
Benzenediazonium cation
Diazonium compounds or diazonium salts are a group of organic compounds sharing a common functional group R−N+
2X−
where R can be any organic group, such as an alkyl or an aryl, and X is an inorganic or organic anion, such as a halogen. Diazonium salts, especially those where R is an aryl group, are important intermediates in the organic synthesis of azo dyes.[1]
Contents
1 Preparation
2 Diazo coupling reactions
3 Displacement of the N2 group
3.1 Replacement by Halogens
3.1.1 Sandmeyer reaction
3.1.2 Gatterman reaction
3.1.3 Replacement by iodide
3.1.4 Replacement by fluoride
3.2 Miscellaneous Replacements
3.2.1 Replacement by hydrogen
3.2.2 Replacement by a hydroxyl group
3.2.3 Replacement by a nitro group
3.2.4 Replacement by a cyano group
3.2.5 Replacement by a thiol group
3.2.6 Replacement by an aryl group
3.2.7 Replacement by a carboxyl group
4 Meerwein reaction
5 Metal complexes
6 Other methods for dediazotization
7 Grafting reactions
8 Reduction to a hydrazine group
9 Applications
9.1 Other uses
10 Safety
11 See also
12 References
13 External links
Preparation[edit]
The process of forming diazonium compounds is called "diazotation", "diazoniation", or "diazotization". The reaction was first reported by Peter Griess in 1858, who subsequently discovered several reactions of this new class of compounds. Most commonly, diazonium salts are prepared by treatment of aromatic amines with nitrous acid and additional acid. Usually the nitrous acid is generated in situ (in the same flask) from sodium nitrite and the excess mineral acid (usually aqueous HCl, H2SO4, or HBF4):
ArNH2 + HNO2 + H+ → ArN2+ + 2H2O
Sample of phenyldiazonium tetrafluoroborate.
Aqueous solutions of diazonium chloride salts, traditionally prepared from the aniline, sodium nitrite, and hydrochloric acid, are unstable above 5 °C. However, one can isolate diazonium compounds as tetrafluoroborate or tosylate salts,[2] which are stable solids at room temperature. It is often preferred that the diazonium salt remain in solutions, but they do tend to supersaturate. Operators have been injured or even killed by an unexpected crystallization of the salt followed by its detonation.[3]
Due to these hazards, diazonium compounds are usually not isolated. Instead they are used in situ. This approach is illustrated in the preparation of an arylsulfonyl compound:[4]
Diazo coupling reactions[edit]
The most widely practiced reaction of diazonium salts is azo coupling. In this process, the diazonium compound is attacked by, i.e., coupled to, electron-rich substrates. When the coupling partners are arenes such as anilines and phenols, the process is an example of electrophilic aromatic substitution:
ArN+
2 + Ar′H → ArN2Ar′ + H+
Another commercially important class of coupling partners are acetoacetic amides, as illustrated by the preparation of Pigment Yellow 12, a diarylide pigment.[5]
The resulting azo compounds are often useful dyes and in fact are called azo dyes.[6] The deep colors of the dyes reflects their extended conjugation. For example, the dye called aniline yellow is produced by mixing aniline and cold solution of diazonium salt and then shaking it vigorously. Aniline yellow is obtained as an yellow solid.[7] Similarly, a cold basic solution of Naphthalen-2-ol (Β-naphthol) give the intensely orange-red precipitate.[7] Methyl orange is an example of an azo dye that is used in the laboratory as a pH indicator.
Displacement of the N2 group[edit]
Arenediazonium cations undergo several reactions in which the N2 group is replaced by another group or ion. Some of the major ones are the following.[8][9]

Replacement by Halogens[edit]
Sandmeyer reaction[edit]
Main article: Sandmeyer reaction
Benzenediazonium chloride heated with cuprous chloride or cuprous bromide respectively dissolved in HCl or HBr yield chlorobenzene or bromobenzene, respectively.
C
6H
5N+
2 + CuCl → C6H5Cl + N2 + Cu+
Gatterman reaction[edit]
In the Gatterman reaction, benzenediazonium chloride is warmed with copper powder and HCl or HBr to produce chlorobenzene and bromobenzene respectively. It is named after the German chemist Ludwig Gattermann.[10]
C
6H
5N+
2 + CuX → C6H5X + N2 + Cu+
Replacement by iodide[edit]
Iodine is not easily introduced into the benzene ring directly. However it can be introduced by treating aryldiazonium cations with potassium iodide:
C
6H
5N+
2 + KI → C6H5I + K+ + N2
Replacement by fluoride[edit]
Main article: Schiemann reaction
Fluorobenzene is produced by thermal decomposition of benzenediazonium fluoroborate. The conversion is called the Balz-Schiemann reaction.[11]
[C
6H
5N+
2]BF−
4 → C6H5F + BF3 + N2
Miscellaneous Replacements[edit]
Replacement by hydrogen[edit]
Arenediazonium cations are reduced by hypophosphorous acid or sodium stannite gives benzene:
[C
6H
5N+
2]Cl− + H3PO2 + H2O → C6H6 + N2 + H3PO3 + HCl
Replacement by a hydroxyl group[edit]
Phenols are produced by heating aqueous solutions of aryldiazonium salts to 100 °C.
C
6H
5N+
2 + H2O → C6H5OH + N2 + H+
This reaction goes by the German name Phenolverkochung ("cooking down to yield phenols"). The phenol formed may react with the diazonium salt and hence the reaction is carried in the presence of an acid which helps in suppressing this further reaction.
Replacement by a nitro group[edit]
Nitrobenzene can be obtained by treating benzenediazonium fluoroborate with sodium nitrite in presence of copper. Alternatively, the diazotisation of the aniline can be conducted in presence of cuprous oxide, which generates cuprous nitrite in situ:
C
6H
5N+
2 + CuNO2 → C6H5NO2 + N2 + Cu+
Replacement by a cyano group[edit]
The cyano group usually cannot be introduced by nucleophilic substitution of haloarenes, but such compounds can be easily prepared from diazonium salts. Illustrative is the preparation of benzonitrile using the reagent cuprous cyanide:
C
6H
5N+
2 + CuCN → C6H5CN + Cu+ + N2
This reaction is a special type of Sandmeyer reaction.
Replacement by a thiol group[edit]
Further information: Leuckart thiophenol reaction
Diazonium salts can be converted to thiols in a two-step procedure. Treatment of benzenediazonium chloride with potassium ethylxanthate followed by hydrolysis of the intermediate xanthate ester gives thiophenol:
C
6H
5N+
2 + C
2H
5OCS−
2 → C6H5SC(S)OC2H5
C6H5SC(S)OC2H5 + H2O → C6H5SH + HOC(S)OC2H5
Replacement by an aryl group[edit]
The aryl group can be coupled to another using aryldiazonium salts. For example, treatment of benzenediazonium chloride with benzene (an aromatic compound) in the presence of sodium hydroxide gives diphenyl:
[C
6H
5N+
2]Cl− + C6H6 → C6H5−C6H5 + N2 + HCl
This reaction is known as the Gomberg–Bachmann reaction. A similar conversion is also achieved by treating benzenediazonium chloride with ethanol and copper powder.
Replacement by a carboxyl group[edit]
Diazonium fluoroborates react with an aliphatic carboxylic acid yield the corresponding benzoic acid. This reaction provides a method to prepare aromatic carboxylic acids from aliphatic carboxylic acids:[citation needed]
[C
6H
5N+
2]BF−
4 + RCO2H → C6H5CO2H + BF3 + N2 + RF
Meerwein reaction[edit]
Benzenediazonium chloride reacts with compounds containing activated double bonds to produces phenylated products. The reaction is called the Meerwein arylation:
[C
6H
5N+
2]Cl− + ArCH=CHCO2H → ArC=C−C6H5 + N2 + CO2 + HCl
Metal complexes[edit]
In their reactions with metal complexes, diazonium cations behave similarly to NO+. For example, low-valent metal complexes add with diazonium salts. Illustrative complexes are [Fe(CO)2(PPh3)2(N2Ph)]+ and the chiral-at-metal complex Fe(CO)(NO)(PPh3)(N2Ph).[12]
Other methods for dediazotization[edit]
by organic reduction at an electrode
by mild reducing agents such as ascorbic acid (vitamin C)[13]
by gamma radiation from solvated electrons generated in water
photoinduced electron transfer
reduction by metal cations, most commonly a cuprous salt.
anion-induced dediazoniation: a counterion such as iodine gives electron transfer to the diazonium cation forming the aryl radical and an iodine radical
solvent-induced dediazoniation with solvent serving as electron donor
Grafting reactions[edit]
In a potential application in nanotechnology, the diazonium salts 4-chlorobenzenediazonium tetrafluoroborate very efficiently functionalizes single wall nanotubes.[14] In order to exfoliate the nanotubes, they are mixed with an ionic liquid in a mortar and pestle. The diazonium salt is added together with potassium carbonate, and after grinding the mixture at room temperature the surface of the nanotubes are covered with chlorophenyl groups with an efficiency of 1 in 44 carbon atoms. These added subsituents prevent the tubes from forming intimate bundles due to large cohesive forces between them, which is a recurring problem in nanotube technology.
It is also possible to functionalize silicon wafers with diazonium salts forming an aryl monolayer. In one study, the silicon surface is washed with ammonium hydrogen fluoride leaving it covered with silicon–hydrogen bonds (hydride passivation).[15] The reaction of the surface with a solution of diazonium salt in acetonitrile for 2 hours in the dark is a spontaneous process through a free radical mechanism:[16]
So far grafting of diazonium salts on metals has been accomplished on iron, cobalt, nickel, platinum, palladium, zinc, copper and gold surfaces. Also grafting to diamond surfaces has been reported.[17] One interesting question raised is the actual positioning on the aryl group on the surface. An in silico study [18] demonstrates that in the period 4 elements from titanium to copper the binding energy decreases from left to right because the number of d-electrons increases. The metals to the left of iron are positioned tilted towards or flat on the surface favoring metal to carbon pi bond formation and those on the right of iron are positioned in an upright position, favoring metal to carbon sigma bond formation. This also explains why diazonium salt grafting thus far has been possible with those metals to right of iron in the periodic table.
Reduction to a hydrazine group[edit]
Diazonium salts can be reduced with stannous chloride (SnCl2) to the corresponding hydrazine derivatives. This reaction is particularly useful in the Fischer indole synthesis of triptan compounds and indometacin. The use of sodium dithionite is an improvement over stannous chloride since it is a cheaper reducing agent with fewer environmental problems.
Applications[edit]
The first use of diazonium salts was to produce water-fast dyed fabrics by immersing the fabric in an aqueous solution of the diazonium compound, followed by immersion in a solution of the coupler (the electron-rich ring that undergoes electrophilic substitution). The major applications of diazonium compounds remains in the dye and pigment industry.[6]
Other uses[edit]
Diazonium compounds are standard reagents used in synthesis of organic compounds, especially aryl derivatives.
Diazonium salts are light sensitive and break down under near UV or violet light. This property has led to their use in document reproduction. In this process, paper or film is coated with a diazonium salt. After contact exposure under light, the residual diazo is converted to a stable azo dye with an aqueous solution of coupler. A more common process uses a paper coated with diazo, coupler and an acid to inhibit coupling; after exposure the image is developed by a vapor mixture of ammonia and water which forces coupling.
Safety[edit]
Solid diazonium halides are often dangerously explosive, and fatalities and injuries have been reported.[3]
The nature of the anions affects stability of the salt. Aryl diazonium perchlorates, such as nitrobenzenediazonium perchlorate, have been used to initiate explosives.
See also[edit]
Diazo
Benzenediazonium chloride
Triazene cleavage
Dinitrogen complex
References[edit]
Jump up ^ Chemistry of the Diazonium and Diazo Groups: Part 1. S. Patai, Ed. 1978 Wiley-Blackwell. ISBN 0-471-99492-8. Chemistry of the Diazonium and Diazo Groups: Part 2. S. Patai, Ed. 1978 Wiley-Blackwell. ISBN 0-471-99493-6.
Jump up ^ Filimonov, Victor D.; Trusova, Marina; Postnikov, Pavel; Krasnokutskaya, Elena A.; Lee, Young Min; Hwang, Ho Yun; Kim, Hyunuk; Chi, Ki-Whan (2008-09-18). "Unusually Stable, Versatile, and Pure Arenediazonium Tosylates: Their Preparation, Structures, and Synthetic Applicability". Organic Letters. 10 (18): 3961–3964. doi:10.1021/ol8013528. ISSN 1523-7060.
^ Jump up to: a b "UK CRHF Incident Report - Supersaturated Diazonium salt causes Fatality". Retrieved 13 May 2010.
Jump up ^ R. V. Hoffman (1981). "m-Trifluoromethylbenzenesulfonyl Chloride". Org. Synth. 60: 121. doi:10.15227/orgsyn.060.0121.
Jump up ^ K. Hunger. W. Herbst "Pigments, Organic" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2012. doi:10.1002/14356007.a20_371
^ Jump up to: a b Klaus Hunger, Peter Mischke, Wolfgang Rieper, et al. "Azo Dyes" in Ullmann’s Encyclopedia of Industrial Chemistry, 2005, Wiley-VCH, Weinheim. doi:10.1002/14356007.a03_245.
^ Jump up to: a b Clark, Jim. "chemguide". Retrieved 28 September 2011.
Jump up ^ March, J. “Advanced Organic Chemistry” 4th Ed. J. Wiley and Sons, 1992: New York. ISBN 978-0-471-60180-7.
Jump up ^ Marye Anne Fox; James K. Whitesell (2004). Organic Chemistry (3, illustrated ed.). Jones & Bartlett Learning. pp. 535–538. ISBN 978-0-7637-2197-8.
Jump up ^ L. Gattermann (1894). "Untersuchungen über Diazoverbindungen". Berichte der deutschen chemischen Gesellschaft. 23 (1): 1218–1228. doi:10.1002/cber.189002301199.
Jump up ^ Flood, D. T. (1933). "Fluorobenzene". Org. Synth. 13: 46. doi:10.15227/orgsyn.013.0046. .
Jump up ^ Sutton, D (1993). "Organometallic Diazo Compounds". Chem. Rev. 93: 905–1022. doi:10.1021/cr00019a008.
Jump up ^ Pinacho Crisóstomo Fernando (2014). "Ascorbic Acid as an Initiator for the Direct C-H Arylation of (Hetero)arenes with Anilines Nitrosated In Situ". Angewandte Chemie International Edition. 53: 2181–2185. doi:10.1002/anie.201309761.
Jump up ^ Green Chemical Functionalization of Single-Walled Carbon Nanotubes in Ionic Liquids B. Katherine Price, Jared L. Hudson, and James M. Tour J. Am. Chem. Soc.; 2005; 127(42) pp. 14867–14870. doi:10.1021/ja053998c
Jump up ^ Michael P. Stewart; Francisco Maya; Dmitry V. Kosynkin; et al. (2004). "Direct Covalent Grafting of Conjugated Molecules onto Si, GaAs, and Pd Surfaces from Aryldiazonium Salts". J. Am. Chem. Soc. 126 (1): 370–8. doi:10.1021/ja0383120. PMID 14709104.
Jump up ^ Reaction sequence: silicon surface reaction with ammonium hydrogen fluoride creates hydride layer. An electron is transferred from the silicon surface to the diazonium salt in an open circuit potential reduction leaving a silicon radical cation and a diazonium radical. In the next step a proton and a nitrogen molecule are expelled and the two radical residues recombine creating a surface silicon to carbon bond.
Jump up ^ S.Q. Lud; M. Steenackers; P. Bruno; et al. (2006). "Chemical Grafting of Biphenyl Self-Assembled Monolayers on Ultrananocrystalline Diamond". J. Am. Chem. Soc. 128 (51): 16884–91. doi:10.1021/ja0657049. PMID 17177439.
Jump up ^ De-en Jiang; Bobby G. Sumpter; Sheng Dai (2006). "Structure and Bonding between an Aryl Group and Metal Surfaces". J. Am. Chem. Soc. 128 (18): 6030–1. doi:10.1021/ja061439f. PMID 16669660.
External links[edit]
W. Reusch. "Reactions of Amines". VirtualText of Organic Chemistry. Michigan State University. Archived from the original on 2012-12-12.
Retrieved from "https://en.wikipedia.org/w/index.php?title=Diazonium_compound&oldid=854709917"
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