Volume 20, Issue 22
Preparative Organic Chemistry
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ChemInform Abstract: New Organocopper Reagents Prepared Utilizing Highly Reactive Copper.

R. D. RIEKE

R. D. RIEKE

Dep. Chem., Univ. Nebr., Lincoln, NE 68588, USA

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R. M. WEHMEYER

R. M. WEHMEYER

Dep. Chem., Univ. Nebr., Lincoln, NE 68588, USA

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T.-C. WU

T.-C. WU

Dep. Chem., Univ. Nebr., Lincoln, NE 68588, USA

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G. W. EBERT

G. W. EBERT

Dep. Chem., Univ. Nebr., Lincoln, NE 68588, USA

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First published: May 30, 1989

Abstract

Highly reactive copper solutions are prepared by one of the methods A) or B) outlined in the scheme.

ChemInform Abstract

Highly reactive copper solutions are prepared by one of the methods A) or B) outlined in the scheme. These activated copper solutions react with organic halides such as (I), (IV), or (VIII) to form stable organocopper reagents which undergo various reactions typical of other organocopper species. For instance, functionalized ketones such as (III) can be prepared (12 examples given overall); conjugate addition reactions provide alkylated cyclohexanones such as (VI) or, similarly, (VII); intermolecular epoxide-opening reactions give alcohols such as (X) (8 examples); finally, intramolecular epoxide ring-opening affords cycloalkylalcohols such as (XII) and (XIII) (9 examples).

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