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Steroids and sex hormones. Part 262 . The radical induced stannane reduction of selenoesters and selenocarbonates: A new method for the degradation of carboxylic acids to nor‐alkanes and for desoxygenation of alcohols to alkanes
Author(s) -
Pfenninger Johannes,
Heuberger Christoph,
Graf Walter
Publication year - 1980
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19800630823
Subject(s) - chemistry , stannane , tributyltin hydride , aldehyde , alcohol , yield (engineering) , organic chemistry , formate , carboxylic acid , acetaldehyde , alkane , medicinal chemistry , photochemistry , ethanol , catalysis , materials science , metallurgy
Esters of carboselenoic acids, formed from carboxylic acids by conventional methods, undergo reaction with tributyltin hydride in inert aromatic solvents, either by heating to give the corresponding aldehyde or the corresponding alkane depending on reaction temperature and the structure of the parent carboxylic acid, or by ultraviolet irradiation at ambient temperature when the aldehyde is formed predominantly in high yield. In the case of esters of α, β‐unsaturated carboselenoic acids the thermal reaction leads only to the corresponding aldehyde. The above stannane reduction can also be applied to selenocarbonates of primary and secondary alcohols (prepared from the corresponding chloroformates), to give the alkane, the parent alcohol and the corresponding formate, in relative amounts depending on the reaction temperature. These reactions thus constitute preparatively useful and high‐yield degradation methods compatible with the presence of many other functional groups.