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
文献索引：Tanaka,R. et al. Tetrahedron, 1971 , vol. 27, p. 2651 - 2669
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- ...
