The Journal of Organic Chemistry

Ammonolysis of vicinal acetoxy chlorides

SJ Lapporte, LL Ferstandig

Index: Lapporte,S.J.; Ferstandig,L.L. Journal of Organic Chemistry, 1961 , vol. 26, p. 3681 - 3685

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Citation Number: 7

Abstract

Ammonolyses of vicinal acetoxy chlorides proceed more readily than the related vicinal dichlorides. Surprisingly, in anhydrous ammonia at 220, the principal product is vicinal diol; trans-2-acetoxycyclohexyl chloride giving a 77% yield of cis-1, 2-cyclohexanediol. A reversal occurs with aqueous ammonia; an 81% yield of trans-2-aminocyclohexanol was isolated. The distribution of products is attributed to a competition between ester ammonolysis and ...

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