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

J. G. A. Kooyman, H. P. G. Hendriks, P. P. Montijn, Lambert Brandsma, J. F. Arens

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Abstract

Abstract Disubstituted acetylenes C4H9C≡CR are produced in the reaction of 1‐ethoxy‐1‐hexyne C4H9C≡COC2H5 with organolithium or Grignard compounds RLi or RMgBr. The yields are moderate to satisfactory. Ethoxyethyne HC≡COC2H5 and phenyllithium C6H5Li afford phenylacetylene HC≡CC6H5 (after hydrolysis) in moderate yield. The formation of acetylenes probably proceeds by an addition‐elimination mechanism.

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Abstract Disubstituted acetylenes C4H9C≡CR are produced in the reaction of 1‐ethoxy‐1‐hexyne C4H9C≡COC2H5 with organolithium or Grignard compounds RLi or RMgBr. The yields are moderate to satisfactory. Ethoxyethyne HC≡COC2H5 and phenyllithium C6H5Li afford phenylacetylene HC≡CC6H5 (after hydrolysis) in moderate yield. The formation of acetylenes probably proceeds by an addition‐elimination mechanism.

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Available abstract

Abstract Disubstituted acetylenes C4H9C≡CR are produced in the reaction of 1‐ethoxy‐1‐hexyne C4H9C≡COC2H5 with organolithium or Grignard compounds RLi or RMgBr. The yields are moderate to satisfactory. Ethoxyethyne HC≡COC2H5 and phenyllithium C6H5Li afford phenylacetylene HC≡CC6H5 (after hydrolysis) in moderate yield. The formation of acetylenes probably proceeds by an addition‐elimination mechanism.

Key concepts: Phenyllithium, Phenylacetylene, Organolithium compounds, Chemistry, Medicinal chemistry, Yield (engineering), Hydrolysis, Ether

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