William D. Emmons: Difference between revisions
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{{Short description|American chemist}} |
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{{Infobox scientist |
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}}'''William D. Emmons''' (November 18, 1924 – December 8, 2001) was an American chemist and published with [[William S. Wadsworth]] a modification to the [[Wittig-Horner reaction]] using phosphonate-stabilized carbanions, now called the [[Horner-Wadsworth-Emmons reaction]] or '''HWE reaction''' or '''Horner-Wittig reaction''' |
}}'''William D. Emmons''' (November 18, 1924 – December 8, 2001) was an American chemist and published with [[William S. Wadsworth]] a modification to the [[Wittig-Horner reaction]] using phosphonate-stabilized carbanions, now called the [[Horner-Wadsworth-Emmons reaction]] or '''HWE reaction''' or '''Horner-Wittig reaction'''. |
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==Life== |
==Life== |
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Emmons studied at the [[University of Minnesota]] and served in the Pacific in [[World War II]] |
Emmons studied at the [[University of Minnesota]] and served in the Pacific in [[World War II]]. He avoided being drafted for the [[Korean War]] by working for the Redstone Arsenal Research of [[Rohm and Haas]] where he worked until his retirement in 1989. |
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==Work== |
==Work== |
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In work undertaken in collaboration with [[Arthur F. Ferris]], Emmons reported that ''in situ'' generated [[trifluoroperacetic acid]] was capable of oxidising [[aniline]] to [[nitrobenzene]],<ref>{{cite journal|title = Oxidation Reactions with Pertrifluoroacetic Acid|first1 = William D.|last1 = Emmons|first2 = Arthur F.|last2 = Ferris|authorlink1 = William D. Emmons|journal = [[J. Am. Chem. Soc.]]|year = 1953|volume = 75|issue = 18|pages = 4623–4624|doi = 10.1021/ja01114a539}}</ref><ref>{{cite journal|title = Peroxytrifluoroacetic Acid. II. The Oxidation of Anilines to Nitrobenzenes|first = William D.|last = Emmons|authorlink = William D. Emmons|journal = [[J. Am. Chem. Soc.]]|year = 1954|volume = 76|issue = 13|pages = 3470–3472|doi = 10.1021/ja01642a030}}</ref> an observation which pioneered the applications of this [[peroxy acid]] as an [[oxidising agent]] in organic chemistry.<ref name = FinOChem>{{cite book|pages = 242–243|chapter = Functional Compounds Containing Oxygen, Sulphur or Nitrogen and their Derivatives|url = https://books.google.com |
In work undertaken in collaboration with [[Arthur F. Ferris]], Emmons reported that ''in situ'' generated [[trifluoroperacetic acid]] was capable of oxidising [[aniline]] to [[nitrobenzene]],<ref>{{cite journal|title = Oxidation Reactions with Pertrifluoroacetic Acid|first1 = William D.|last1 = Emmons|first2 = Arthur F.|last2 = Ferris|authorlink1 = William D. Emmons|journal = [[J. Am. Chem. Soc.]]|year = 1953|volume = 75|issue = 18|pages = 4623–4624|doi = 10.1021/ja01114a539}}</ref><ref>{{cite journal|title = Peroxytrifluoroacetic Acid. II. The Oxidation of Anilines to Nitrobenzenes|first = William D.|last = Emmons|authorlink = William D. Emmons|journal = [[J. Am. Chem. Soc.]]|year = 1954|volume = 76|issue = 13|pages = 3470–3472|doi = 10.1021/ja01642a030}}</ref> an observation which pioneered the applications of this [[peroxy acid]] as an [[oxidising agent]] in organic chemistry.<ref name = FinOChem>{{cite book|pages = 242–243|chapter = Functional Compounds Containing Oxygen, Sulphur or Nitrogen and their Derivatives|chapter-url = https://books.google.com/books?id=XE5VHh7uL_0C&pg=PA242|title = Fluorine in Organic Chemistry|first = Richard D.|last = Chambers|publisher = [[CRC Press]]|year = 2004|isbn = 9780849317903}}</ref> Emmons went on to discuss the preparation of trifluoroperacetic acid<ref name = TFPAAprep /> and numerous applications of the new reagent, including:<ref name = FinOChem /> oxidation of [[nitrosamine]]s to [[nitramine]]s;<ref name = TFPAAprep>{{cite journal|title = Peroxytrifluoroacetic Acid. I. The Oxidation of Nitrosamines to Nitramines|first = William D.|last = Emmons|authorlink = William D. Emmons|journal = [[J. Am. Chem. Soc.]]|year = 1954|volume = 76|issue = 13|pages = 3468–3470|doi = 10.1021/ja01642a029}}</ref> the [[Baeyer–Villiger oxidation]]s of [[ketone]]s to [[ester]]s;<ref>{{cite journal|title = Peroxytrifluoroacetic Acid. V. The Oxidation of Ketones to Esters|first1 = William D.|last1 = Emmons|authorlink1 = William D. Emmons|first2 = George B.|last2 = Lucas|journal = [[J. Am. Chem. Soc.]]|year = 1955|volume = 77|issue = 8|pages = 2287–2288|doi = 10.1021/ja01613a077}}</ref> and the conversion of [[alkene]]s to [[epoxide]]s (in the presence of a buffer)<ref>{{cite journal|title = Peroxytrifluoroacetic Acid. IV. The Epoxidation of Olefins|first1 = William D.|last1 = Emmons|authorlink1 = William D. Emmons|first2 = Angelo S.|last2 = Pagano|journal = [[J. Am. Chem. Soc.]]|year = 1955|volume = 77|issue = 1|pages = 89–92|doi = 10.1021/ja01606a029}}</ref> or to [[glycol]]s (without the buffer).<ref>{{cite journal|title = Peroxytrifluoroacetic Acid. III. The Hydroxylation of Olefins|authorlink1 = William D. Emmons|first1 = William D.|last1 = Emmons|first2 = Angelo S.|last2 = Pagano|first3 = Jeremiah P.|last3 = Freeman|journal = [[J. Am. Chem. Soc.]]|year = 1954|volume = 76|issue = 13|pages = 3472–3474|doi = 10.1021/ja01642a031}}</ref> |
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==References== |
==References== |
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{{Reflist}} |
{{Reflist}} |
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* {{cite journal|url = http://www.orgsyn.org/content/pdfs/obits/emmons.pdf|title = William D. Emmons: November 18, 1924 - December 8, 2001|first = Jeremiah P.|last = Freeman|journal = [[Org. Synth.]]|volume = 80|pages = xxvii-xxix|date = November 14, 2002}} |
* {{cite journal|url = http://www.orgsyn.org/content/pdfs/obits/emmons.pdf|title = William D. Emmons: November 18, 1924 - December 8, 2001|first = Jeremiah P.|last = Freeman|journal = [[Org. Synth.]]|volume = 80|pages = xxvii-xxix|date = November 14, 2002}} |
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{{DEFAULTSORT:Emmons, William D.}} |
{{DEFAULTSORT:Emmons, William D.}} |
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[[Category:2001 deaths]] |
[[Category:2001 deaths]] |
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[[Category:University of Minnesota alumni]] |
[[Category:University of Minnesota alumni]] |
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[[Category:American chemists]] |
[[Category:20th-century American chemists]] |
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[[Category:American military personnel of World War II]] |
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Latest revision as of 10:56, 10 March 2023
William D. Emmons | |
|---|---|
| Born | November 18, 1924 |
| Died | December 8, 2001 (aged 77) |
| Nationality | American |
| Alma mater | University of Minnesota |
| Known for | Horner-Wadsworth-Emmons reaction |
| Scientific career | |
| Institutions | Rohm and Haas |
William D. Emmons (November 18, 1924 – December 8, 2001) was an American chemist and published with William S. Wadsworth a modification to the Wittig-Horner reaction using phosphonate-stabilized carbanions, now called the Horner-Wadsworth-Emmons reaction or HWE reaction or Horner-Wittig reaction.
Life[edit]
Emmons studied at the University of Minnesota and served in the Pacific in World War II. He avoided being drafted for the Korean War by working for the Redstone Arsenal Research of Rohm and Haas where he worked until his retirement in 1989.
Work[edit]
In work undertaken in collaboration with Arthur F. Ferris, Emmons reported that in situ generated trifluoroperacetic acid was capable of oxidising aniline to nitrobenzene,[1][2] an observation which pioneered the applications of this peroxy acid as an oxidising agent in organic chemistry.[3] Emmons went on to discuss the preparation of trifluoroperacetic acid[4] and numerous applications of the new reagent, including:[3] oxidation of nitrosamines to nitramines;[4] the Baeyer–Villiger oxidations of ketones to esters;[5] and the conversion of alkenes to epoxides (in the presence of a buffer)[6] or to glycols (without the buffer).[7]
References[edit]
- ^ Emmons, William D.; Ferris, Arthur F. (1953). "Oxidation Reactions with Pertrifluoroacetic Acid". J. Am. Chem. Soc. 75 (18): 4623–4624. doi:10.1021/ja01114a539.
- ^ Emmons, William D. (1954). "Peroxytrifluoroacetic Acid. II. The Oxidation of Anilines to Nitrobenzenes". J. Am. Chem. Soc. 76 (13): 3470–3472. doi:10.1021/ja01642a030.
- ^ a b Chambers, Richard D. (2004). "Functional Compounds Containing Oxygen, Sulphur or Nitrogen and their Derivatives". Fluorine in Organic Chemistry. CRC Press. pp. 242–243. ISBN 9780849317903.
- ^ a b Emmons, William D. (1954). "Peroxytrifluoroacetic Acid. I. The Oxidation of Nitrosamines to Nitramines". J. Am. Chem. Soc. 76 (13): 3468–3470. doi:10.1021/ja01642a029.
- ^ Emmons, William D.; Lucas, George B. (1955). "Peroxytrifluoroacetic Acid. V. The Oxidation of Ketones to Esters". J. Am. Chem. Soc. 77 (8): 2287–2288. doi:10.1021/ja01613a077.
- ^ Emmons, William D.; Pagano, Angelo S. (1955). "Peroxytrifluoroacetic Acid. IV. The Epoxidation of Olefins". J. Am. Chem. Soc. 77 (1): 89–92. doi:10.1021/ja01606a029.
- ^ Emmons, William D.; Pagano, Angelo S.; Freeman, Jeremiah P. (1954). "Peroxytrifluoroacetic Acid. III. The Hydroxylation of Olefins". J. Am. Chem. Soc. 76 (13): 3472–3474. doi:10.1021/ja01642a031.
- Freeman, Jeremiah P. (November 14, 2002). "William D. Emmons: November 18, 1924 - December 8, 2001" (PDF). Org. Synth. 80: xxvii–xxix.
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