Journal of Organic Chemistry p. 4880 - 4885 (1981)
Update date:2022-08-05
Topics:
Ayral-Kaloustian, Semiramis
Agosta, William C.
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 deg C, 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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