Vinylmetalloids. II. The high regioselectivity of dialkylboranes in the hydroboration of vinyltrimethylsilane

John A. Soderquist, Alfred Hassner

Research output: Contribution to journalArticlepeer-review

29 Scopus citations

Abstract

Dialkylboranes such as disiamylborane, dicyclohexylborane and 9-borabicyclo[3.3.1]nonane add cleanly to vinyltrimethylsilane (I) with high regiospecificity (≥ 95%) to give the corresponding β-silylethylboranes, valuable intermediates in the synthesis of functionalized organosilanes. Oxidation of these adducts provides a convenient, high-yield route to 2-trimethylsilylethanol (IIβ). Reduction of acetyltrimethylsilane (IX) with borane-tetrahydrofuran provides a simple route to the isomeric 1-trimethylsilylethanol (IIα). These new developments illustrate the utility of borane reagents in the regiospecific syntheses of trimethylsilylethanols (II).

Original languageEnglish
Pages (from-to)C12-C16
JournalJournal of Organometallic Chemistry
Volume156
Issue number1
DOIs
StatePublished - 15 Aug 1978
Externally publishedYes

Bibliographical note

Funding Information:
The stimulating conversations and helpful suggestions of Professor H.C. Brown, Dr. J.L. Hubbard, Dr. S. Krishnamurthy, Mr. J. Campbell, Mr. S.U. Kulkarni, Mr. K.L. Thompson and Mr. K.K. Wang regarding this work are gratefully acknowledged. Support for this work from NC1 Grant CA-19203 and NSF Grant CHE-76-20846 is appreciated.

Funding

The stimulating conversations and helpful suggestions of Professor H.C. Brown, Dr. J.L. Hubbard, Dr. S. Krishnamurthy, Mr. J. Campbell, Mr. S.U. Kulkarni, Mr. K.L. Thompson and Mr. K.K. Wang regarding this work are gratefully acknowledged. Support for this work from NC1 Grant CA-19203 and NSF Grant CHE-76-20846 is appreciated.

FundersFunder number
NC1CA-19203
National Science FoundationCHE-76-20846

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