Prototropic rearrangement in reactions of 4-alkoxy-3-chloro-1-butanols with bases

K Poisel, F Krejča, J Jonas

Index: Poisel,K. et al. Collection of Czechoslovak Chemical Communications, 1978 , vol. 43, p. 876 - 883

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Abstract

Reaction of 4-alkoxy-2-chloro-l-butanols (1) and their acetates II with bases depends on the base and reaction conditions employed and affords complex mixtures of fragmentation products or mixtures of 4-alkoxy-2-buten-l-ols (III) and 4-alkoxy-3-buten-l-ols (IV) or almost pure trans-IV. Hydrogenolysis of 2, 5-dihydro-2, 5-dimethoxyfuran (V) by chloroalane leads to trans--4-methoxy-2-buten-l-ol (trans-IlIa). Vinyl ethers IV undergo an acid-catalyzed ...