Volume 22, Issue 16
Heterocyclic Compounds
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ChemInform Abstract: α-Sulfinyl-Substituted Radicals. Part 1. Stereoselective Radical Addition Reactions of Cyclic α-Sulfinyl Radicals.

A. WALDNER

A. WALDNER

Cent. Res. Lab., Ciba-Geigy AG, CH-4002 Basel, Switz.

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A. DE MESMAEKER

A. DE MESMAEKER

Cent. Res. Lab., Ciba-Geigy AG, CH-4002 Basel, Switz.

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P. HOFFMANN

P. HOFFMANN

Cent. Res. Lab., Ciba-Geigy AG, CH-4002 Basel, Switz.

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T. MINDT

T. MINDT

Cent. Res. Lab., Ciba-Geigy AG, CH-4002 Basel, Switz.

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T. WINKLER

T. WINKLER

Cent. Res. Lab., Ciba-Geigy AG, CH-4002 Basel, Switz.

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First published: April 23, 1991

Abstract

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ChemInform Abstract

Enantiomerically pure 3-oxo-2-(1-phenylethyl)-5-isothiazolidinyl 1-oxide radicals, prepared from the 5-phenylseleno compound (III), undergo addition reactions with the (2-alkenyl)tributylstannanes (IV) to give the 5-(2-alkenyl)-2-(1-phenylethyl)-3-isothiazolidone 1-oxides (V) and (VI) with predominance of the former. The diastereoselectivity of these radical additions proves to depend on the hydrogen bridging ability of the solvent. Further examples are described in the original paper.

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