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

Alfred Hassner, John A. Soderquist

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56 Scopus citations

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-silaketones.

Original languageEnglish
Pages (from-to)C1
JournalJournal of Organometallic Chemistry
Volume131
Issue number1
DOIs
StatePublished - 3 May 1977
Externally publishedYes

Bibliographical note

Funding Information:
This work was supported by PHS Grant CA 19203 from Institute.

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