Nucleic acid related compounds. 42. A general procedure for the efficient deoxygenation of secondary alcohols. Regiospecific and stereoselective conversion of …

MJ Robins, JS Wilson, F Hansske

Index: Robins; Wilson; Hansske Journal of the American Chemical Society, 1983 , vol. 105, # 12 p. 4059 - 4065

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Citation Number: 536

Abstract

Abstract: Treatment of unhindered secondary alcohols with phenoxythiocarbonyl chloride (phenyl chlorothionocarbonate) in pyridine/dichloromethane, or in acetonitrile with 4- dimethylaminopyridine catalysis for hindered alcohols, gave clean conversion to their O- phenoxythiocarbonyl derivatives. Reductive deoxygenation of these phenyl thionocarbonate esters proceeded smoothly, using tri-n-butyltin hydride and a free radical initiator in warm ...

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