Reaction of nitriles with thionyl chloride in the presence of hydrogen chloride. Formation of sulfinyl and sulfenyl chlorides and phenyl cyanosulfine

M Ohoka, T Kojitani, S Yanagida…

Index: Ohoka,M. et al. Journal of Organic Chemistry, 1975 , vol. 40, p. 3540 - 3544

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Citation Number: 17

Abstract

Results Reaction of Nitriles Possessing one a Hydrogen. When 2-methylpropionitrile (la) was allowed to react with thionyl chloride (3 equiv) in the presence of an excess of hydrogen chloride (ca. 6 equiv) at Oo for 7 days using diethyl ether as a solvent, a-cyano-a- methylethanesulfinyl chloride (2a) was obtained in 50% yield (based on the nitrile), and 37% of the starting nitrile was recovered.