Volume 20, Issue 22
Preparative Organic Chemistry
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ChemInform Abstract: The Role of BF3·Et2O in Reactions of Lower Order (Gilman) Organocuprates.

B. H. LIPSHUTZ

B. H. LIPSHUTZ

Dep. Chem., Univ. Calif., Santa Barbara, CA 93106, USA

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E. L. ELLSWORTH

E. L. ELLSWORTH

Dep. Chem., Univ. Calif., Santa Barbara, CA 93106, USA

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T. J. SIAHAAN

T. J. SIAHAAN

Dep. Chem., Univ. Calif., Santa Barbara, CA 93106, USA

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First published: May 30, 1989

Abstract

The effects of BF3·Et2O on low order organocuprate reactions in THF are investigated so as to determine what factors are responsible for the oftentimes dramatic reaction-rate enhancements observed.

ChemInform Abstract

The effects of BF3·Et2O on low order organocuprate reactions in THF are investigated so as to determine what factors are responsible for the oftentimes dramatic reaction-rate enhancements observed. From spectroscopic experiments on the reagents alone, supported further by chemical studies, it is found that an originally formed cuprate (e.g. R2CuLi) is altered significantly upon exposure to this Lewis acid. The copper-containing species thereby generated, together with BF3, form a more reactive combination and appear to be at least in part responsible for the accelerated chemistry. Comparative reactions summarized in a table, some examples of which are given in the scheme, illustrate these findings.

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