- Efficient radical oxygenation of α-lodocarboxylic acid derivatives
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(equation presented) Treatment of α-iodocarboxylic acid derivatives with 2 equiv of triethylborane under oxygen atmosphere gives the corresponding α-hydroxy add derivatives This method is based on an iodine atom transfer from the ethyl radical, generated by the reaction of riethylborane and oxygen, with the α-iodocarbonyl compound. It offers several advantages over classical ionic substitution reactions: no elimanation product is observed tertiary iodides are efficiently converted to alcohos, and finally, this one-step procedure is working with substrates sensitive to nucleophiles.
- Kihara, Nobuhiro,Ollivier, Cyril,Renaud, Philippe
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p. 1419 - 1422
(2008/02/09)
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- Preparation of α-Substituted S-Phenyl Thio Esters from Aldehydes and (Phenylthio)nitromethane
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Acetaldehyde and isobutyraldehyde, RCHO, reacted with (phenylthio)nitromethane (KO-t-Bu, THF, t-BuOH) followed by methanesulfonyl chloride (Et3N, CH2Cl2) to give the (Z)-alkenes RCH=C(SPh)NO2.These reacted with the nucleophiles NuM = potassium phthalimid
- Barrett, Anthony G. M.,Graboski, Gregory, G.,Russell, Mark A.
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p. 1012 - 1015
(2007/10/02)
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- Phenylthionitromethane: a Versatile Reagent for the Conversion of Aldehydes into α-Substituted S-Phenyl Thioesters
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Acetaldehyde and isobutyraldehyde, RCHO, reacted with phenylthionitromethane (KOH, MeOH) followed by methanesulphonyl chloride (Et3N, CH2Cl2) to give the alkenes, RCH=C(SPh)NO2; these reacted with the nucleophiles i, potassium
- Banks, Bernard J.,Barrett, Anthony G. M.,Russell, Mark A.
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p. 670 - 671
(2007/10/02)
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