Hunsdiecker reaction

Hunsdiecker reaction

The Hunsdiecker reaction (also called the "Borodin reaction" after Alexander Borodin) is the organic reaction of silver salts of carboxylic acids with halogens to give organic halides. [Cläre Hunsdiecker, "et al." U.S. Patent # 2,176,181.] [Heinz Hunsdiecker; Cläre Hunsdiecker "Ber." 1942, "75", 291.DOI|10.1002/cber.19420750309 ] [Borodin, A. "Ann." 1861, "119", 121.DOI| 10.1002/jlac.18611190113 ] [Allen, C. F. H.; Wilson, C. V. "Organic Syntheses", Coll. Vol. 3, p.578 (1955); Vol. 26, p.52 (1946). ( [http://www.orgsyn.org/orgsyn/prep.asp?prep=cv3p0578 Article] )] The reaction is named after Heinz Hunsdiecker and Cläre Hunsdiecker.

Several reviews have been published.Johnson, R. G.; Ingham, R. K. "Chem. Rev." 1956, "56", 219. (Review)] [Wilson, C. V. "Org. React." 1957, "9", 341. (Review)]

Mercuric oxide will also effect this transformation. [Meek, J. S.; Osuga, D. T. "Organic Syntheses", Coll. Vol. 5, p.126 (1973); Vol. 43, p.9 (1963). ( [http://www.orgsyn.org/orgsyn/prep.asp?prep=cv5p0126 Article] )] [Lampman, G. M.; Aumiller, J. C. "Organic Syntheses", Coll. Vol. 6, p.179 (1988); Vol. 51, p.106 (1971). ( [http://www.orgsyn.org/orgsyn/prep.asp?prep=cv6p0179 Article] )]

Reaction mechanism

The reaction mechanism of the Hunsdiecker reaction is believed to involve organic radical intermediates. The silver salt of the carboxylic acid 1 will quickly react with bromine to form intermediate 2. Formation of the diradical pair 3 allows for radical decarboxylation to form the diradical pair 4, which will quickly recombine to form the desired organic halide 5.

Variations

imonini reaction

The reaction of silver salts of carboxylic acids with iodine is called the Simonini reaction , named after Angelo Simonini a student of Adolf Lieben at the University of Vienna. [cite journal
title = Über den Abbau der fetten Säuren zu kohlenstoffärmeren Alkoholen
author = Simonini, A.
journal = Monatshefte für Chemie
volume = 13
issue = 1
pages = 320–325
year = 1892
url =
doi = 10.1007/BF01523646
] [cite journal
title = Über den Abbau der fetten Säuren zu kohlenstoffärmeren Alkoholen
author = Simonini, A.
journal = Monatshefte für Chemie
volume = 14
issue = 1
pages = 80–92
year = 1893
url =
doi = 10.1007/BF01517859
]

References

ee also

*Barton-McCombie deoxygenation
*Kochi reaction


Wikimedia Foundation. 2010.

Игры ⚽ Поможем написать курсовую

Look at other dictionaries:

  • Hunsdiecker — Heinz Hunsdiecker (* 22. Januar 1904 in Köln; † 22. November 1981 ebenda) war ein deutscher Chemiker. Leben und Werk Hunsdiecker studierte unter Robert Wintgen an der Universität Köln wo er 1929 seinen Doktortitel mit einer Dissertation zum Thema …   Deutsch Wikipedia

  • Réaction de substitution — Une réaction de substitution est une réaction organique dans laquelle un atome ou groupe d atomes (groupe fonctionnel) d un composé chimique est remplacé par un autre atome ou groupe d atomes (le substituant)[1],[2]. Cet article se concentre sur… …   Wikipédia en Français

  • Heinz Hunsdiecker — Born 22 January 1904(1904 01 22) Cologne Germany Died 22 October 1981(1981 10 22) …   Wikipedia

  • Substitution reaction — In a substitution reaction, a functional group in a particular chemical compound is replaced by another group.[1][2] In organic chemistry, the electrophilic and nucleophilic substitution reactions are of prime importance. Organic substitution… …   Wikipedia

  • Free radical reaction — A free radical reaction is any chemical reaction involving free radicals. This reaction type is abundant in organic reactions. Two pioneering studies into free radical reactions have been the discovery of the triphenylmethyl radical by Moses… …   Wikipedia

  • Kochi reaction — The Kochi reaction is an organic reaction for the decarboxylation of carboxylic acids to alkyl halides with lead tetraacetate and a lithium chloride or other lithium salts [ A New Method for Halodecarboxylation of Acids Using Lead(IV) Acetate Jay …   Wikipedia

  • Heinz Hunsdiecker — (* 22. Januar 1904 in Köln; † 22. November 1981 ebenda) war ein deutscher Chemiker. Leben und Werk Hunsdiecker studierte unter Robert Wintgen an der Universität Köln, wo er 1929 seinen Doktortitel mit einer Dissertation zum Thema „Teilchengewicht …   Deutsch Wikipedia

  • Scientific phenomena named after people — This is a list of scientific phenomena and concepts named after people (eponymous phenomena). For other lists of eponyms, see eponym. NOTOC A* Abderhalden ninhydrin reaction Emil Abderhalden * Abney effect, Abney s law of additivity William de… …   Wikipedia

  • Именные реакции в органической химии — В органической химии существует огромное число реакций, носящих имя исследователя, открывшего или исследовавшего данную реакцию. Часто в названии реакции фигурируют имена нескольких ученых: это могут быть авторы первой публикации (например,… …   Википедия

  • 1,3-déshydroadamantane — Propellane de gauche à droite : [1.1.1]propellane, [2.2.2]propellane, 1,3 dehydroadamantane Les propellanes sont une classe d hydrocarbures saturés ou alcanes tricycliques c est à dire avec deux atomes de carbone tête de pont et quatre… …   Wikipédia en Français

Share the article and excerpts

Direct link
Do a right-click on the link above
and select “Copy Link”