Volume 24, Issue 32
Preparative Organic Chemistry
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ChemInform Abstract: Aziridines. Part 61. Ring Opening of 2,2-Dimethyl-1-sulfonylaziridines by Anilines: Regioselectivity and Revised Structure of Main Products.

B. BUCHHOLZ

B. BUCHHOLZ

Pharm.-Chem. Inst., Univ. Heidelberg, W-6900 Heidelberg, Germany

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P.-Y. LIN

P.-Y. LIN

Pharm.-Chem. Inst., Univ. Heidelberg, W-6900 Heidelberg, Germany

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A. ONISTSCHENKO

A. ONISTSCHENKO

Pharm.-Chem. Inst., Univ. Heidelberg, W-6900 Heidelberg, Germany

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H. STAMM

H. STAMM

Pharm.-Chem. Inst., Univ. Heidelberg, W-6900 Heidelberg, Germany

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First published: August 10, 1993

Abstract

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ChemInform Abstract

The title reaction leads to the isomeric products (III) and (IV). Using aniline, the isomers (IIIa)-(IIIc) are obtained as main products. The isomer (IV) formed by attack on position 3 of (I) usually arises in a small or negligible amount which seems to decrease with decreasing basicity of the aniline compound used and to increase with increasing steric demand of the aniline compound. On the basis of the results the mechanism of the reaction is discussed.

chemical structure image

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