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 language | English |
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Pages (from-to) | C12-C16 |
Journal | Journal of Organometallic Chemistry |
Volume | 156 |
Issue number | 1 |
DOIs | |
State | Published - 15 Aug 1978 |
Externally published | Yes |
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.
Funders | Funder number |
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NC1 | CA-19203 |
National Science Foundation | CHE-76-20846 |