Journal of Organometallic Chemistry

Cleavage of α-(phenylthio) alkylboranes with N-chlorosuccinimide. A convenient route to monothioacetals and acetals

A Mendoza, DS Matteson

Index: Mendoza,A.; Matteson,D.S. Journal of Organometallic Chemistry, 1978 , vol. 156, p. 149 - 157

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Abstract

Abstract α-(Phenylthio) alkylboranes, which are easily prepared by two different homologation processes, are deboronated by N-chlorosuccinimide in mildly basic methanol to form monothioacetals or, with excess reagent, dimethyl acetals. Both boronic esters and trialkylboranes react, the latter considerably faster. The reaction is specific for the sulfur- substituted alkylborane group, suggesting that initial chlorination occurs at sulfur. Under ...

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