Tetrahedron

Nucleophilic substitution at an acetylenic carbon: Competing processes in the reactions of sodium methoxide with phenylbromoacetylene or phenylchloroacetylene in …

R Tanaka, M Rodgers, R Simonaitis, SI Miller

Index: Tanaka,R. et al. Tetrahedron, 1971 , vol. 27, p. 2651 - 2669

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Citation Number: 19

Abstract

Phenylhaloacetylenes are triphilic towards methoxide ion in methanol. With phenylchloroacetylene (1′), methoxide attacks∼ 0· 2% on chlorine,∼ 99% on carbon 1, and∼ 1% on carbon 2; with phenylbromoacetylene (1), methoxide attacks∼ 5% on bromine,∼ 83% on carbon 1, and∼ 11% on carbon 2. The first detectable products, phenylacetylene, phenylmethoxyacetylene (2),(E)-β-bromo-β-methoxy-styrene, and (Z)-β- ...