Chemistry of acetylenic ethers: 76 Preparation of compounds with a 1,3‐enyne system

Abstract

Abstract Ethers with the systems , CH 3 CCCH(OR) 2 , CH 3 CCCH(OR) 3 or ‐CH 2 ‐CH 2 ‐CCOR undergo an elimination of ROH [R = alkyl, 2‐alkynyl (‐CH 2 CC‐R′) phenyl, or 2‐tetrahydropyranyl] with formation of 1,3‐enyne derivatives, , on treatment with alkali amides in liquid ammonia. The cyclic ethers: and are isomerized under these conditions to the 1,3‐enyne carbinols HCC‐CHC(CH 3 )CH 2 OH and HCC‐CHCH(CH 2 ) 4 OH.