Preparation of 3-hydroxycyclohexaneacetonitriles

S Ayral-Kaloustian, WC Agosta

Index: Ayral-Kaloustian, Semiramis; Agosta, William C. Journal of Organic Chemistry, 1981 , vol. 46, # 24 p. 4880 - 4885

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Citation Number: 3

Abstract

Preparation of cis-4-tert-butyl-cis-3-hydroxycyclohexaneacetonitrile (2) and the parent cis-3- hydroxycyclohexaneacetonitrile (1) is described. In intermediates leading to 2 severe crowding at axially substituted C (3) leads to unusual reactions, including rapid intramolecular oxonium ion formation at 0-5 OC, abnormally easy hydride reduction of a nitrile, and formation of an open-chain hemiacetal that is relatively stable to aqueous acid.

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