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

Alfred Hassner; John A. Soderquist

doi:10.1016/S0022-328X(00)91369-X

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

Alfred Hassner, John A. Soderquist

State University of New York Binghamton University

Research output: Contribution to journal › Article › peer-review

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 language	English
Pages (from-to)	C1
Journal	Journal of Organometallic Chemistry
Volume	131
Issue number	1
DOIs	https://doi.org/10.1016/S0022-328X(00)91369-X
State	Published - 3 May 1977
Externally published	Yes

Bibliographical note

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

Funding

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

Funders	Funder number
Institute
Presbyterian Historical Society	CA 19203

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10.1016/S0022-328X(00)91369-X

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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.",

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AB - 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.

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

Abstract

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