Journal of Organometallic Chemistry

Synthetic methods: IX. Hydroboration of silylacetylenes. A new synthesis of α-silaketones

A Hassner, JA Soderquist

Index: Hassner,A.; Soderquist,J.A. Journal of Organometallic Chemistry, 1977 , vol. 131, p. C1 - C4

Full Text: HTML

Citation Number: 50

Abstract

Abstract The first example of monohydroboration of silylacetylenes with dichloroborane is described. The reaction occurs regio-and stereo-specifically and leads after methanolysis to isolable vinylboronic esters (III). The latter undergo photo Z⇌ E isomerization. Oxidation of III to the corresponding α-silaketone was accomplished in high yield using trimethylamine-N- oxide dihydrate. The overall method represents a useful conversion of acetylenes to α- ...