Volume 26, Issue 19
Isocyclic Compounds
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ChemInform Abstract: Evidence for Michael-Type Reaction of Alkenyliodonium Salts: Nucleophilic Substitutions with Sodium Benzenesulfinate.

M. OCHIAI

M. OCHIAI

Fac. Pharm. Sci., Univ. Tokushima, Tokushima 770, Japan

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Y. KITAGAWA

Y. KITAGAWA

Fac. Pharm. Sci., Univ. Tokushima, Tokushima 770, Japan

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M. TOYONARI

M. TOYONARI

Fac. Pharm. Sci., Univ. Tokushima, Tokushima 770, Japan

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K. UEMURA

K. UEMURA

Fac. Pharm. Sci., Univ. Tokushima, Tokushima 770, Japan

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First published: May 9, 1995

Abstract

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ChemInform Abstract

The nucleophilic vinylic substitutions of the tetrafluoroborates (I) with sodium benzenesulfinate (II) involve a hitherto unknown Michael- type addition to the Cβ-atom of (I). High yields of the bissulfones (III) are obtained. In contrast, application of the method to the bromo compound (IV) gives considerable amounts of the (Z)- halosulfone (V), a type of product which is obtained from (I) only in trace amounts.

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