Studies on Vinyl Acetals. III:Addition reaction to vinyl acetals

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An addition reaction of various reagents on a double bond of vinyl acetal (1, 1-dialkoxy-3-butene) has been investigated.(1) The addition of hydrogen halides was proceeded without catalyst and at room temperature towards the direction of Markownikoff's rule. The product was β-halobutyraldehyde acetal. The anti-Markownikoff type additive reaction by use of HBr was not successful due to predominance of ionic reaction.(2) Addition of halogen was proceeded smoothly at low temperature but the distillation of product was difficult, probably due to the presence of unstable side-reaction product.(3) Alcohol gave 1, 1, 3-trialkoxybutane by addition in the presence of hydrochloric acid catalyst.(4) Mercaptan gave an addition product composed of 4-alkylmercapto-butyraldehyde acetal with high yield by exposure to ultraviolet light or in the presence of mercuric oxide catalyst. In the presence of hydrochloric acid catalyst, a 3-substituted product was formed by Markownikoff type additive reaction.
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