Volume 29, Issue 1
Preparative Organic Chemistry
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ChemInform Abstract: A Grignard-Type Addition of Allyl Unit to Carbonyl Compounds Containing a Carboxyl Group by Using BiCl3—Zn(0)—Allyl Bromide.

M. WADA

M. WADA

Dep. Chem., Fac. Integr. Arts Sci., Univ. Tokushima, Minamijosanjima, Tokushima 770, Japan

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M. HONNA

M. HONNA

Dep. Chem., Fac. Integr. Arts Sci., Univ. Tokushima, Minamijosanjima, Tokushima 770, Japan

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Y. KURAMOTO

Y. KURAMOTO

Dep. Chem., Fac. Integr. Arts Sci., Univ. Tokushima, Minamijosanjima, Tokushima 770, Japan

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N. MIYOSHI

N. MIYOSHI

Dep. Chem., Fac. Integr. Arts Sci., Univ. Tokushima, Minamijosanjima, Tokushima 770, Japan

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First published: 24 June 2010

Abstract

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ChemInform Abstract

Carbonyl compounds containing a carboxyl group react with allyl bromide to afford the corresponding homoallylic alcohols, e.g. (III), or intramolecular dehydrated lactones such as (VII). The use of BiCl3 is essential in these reactions. The reaction of phenylpropanal (X) with allyl bromide proceeds smoothly under strongly acidic conditions as well as under strongly basic conditions.

chemical structure image

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