Chemistry of acetylenic ethers. Part 89: The reaction of organolithium compounds with 1‐alkynyl ethers

Abstract

Abstract Disubstituted acetylenes C 4 H 9 C≡CR are produced in the reaction of 1‐ethoxy‐1‐hexyne C 4 H 9 C≡COC 2 H 5 with organolithium or Grignard compounds RLi or RMgBr. The yields are moderate to satisfactory. Ethoxyethyne HC≡COC 2 H 5 and phenyllithium C 6 H 5 Li afford phenylacetylene HC≡CC 6 H 5 (after hydrolysis) in moderate yield. The formation of acetylenes probably proceeds by an addition‐elimination mechanism.