The invention of radical reactions. Part XXXI. Diphenylsilane: A reagent for deoxygenation of alcohols via their thiocarbonyl derivatives, deamination via isonitriles, and dehalogenation of bromo- and iodo- compounds by radical chain chemistry
Various thionocarbonates and xanthates of alcohols and bis-xanthates of vic-diols are readily deoxygenated to the corresponding hydrocarbons or olefins, while bromides and iodides are dehalogenated with diphenylphenylsilane in good yield.
Barton, Derek H. R.,Jang, Doo Ok,Jaszberenyi, Joseph Cs.
The invention of radical reactions. Part XXIV. Relative rates of acylation and radical deoxygenation of secondary alcohols
Secondary alcohols were transformed into various thiocarbonyl derivatives. Reduction of these compounds using tributyltin hydride and an initiator afforded the corresponding deoxy-compounds. Half-life and competitive measurements showed that all these reactions were fast and could be run to completion.
Barton,Dorchak,Jaszberenyi
p. 7435 - 7446
(2007/10/02)
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