Volume 33, Issue 8
Preparative Organic Chemistry
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ChemInform Abstract: The Stereospecific Addition of Hydroxylamines to α,β-Unsaturated Sulfones, Nitriles and Nitro Compounds.

Ian A. O'Neil

Ian A. O'Neil

Dep. Chem., Univ. Liverpool, Liverpool L69 7ZD, UK

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Ed Cleator

Ed Cleator

Dep. Chem., Univ. Liverpool, Liverpool L69 7ZD, UK

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J. Mike Southern

J. Mike Southern

Dep. Chem., Univ. Liverpool, Liverpool L69 7ZD, UK

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Jamie F. Bickley

Jamie F. Bickley

Dep. Chem., Univ. Liverpool, Liverpool L69 7ZD, UK

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David J. Tapolczay

David J. Tapolczay

Dep. Chem., Univ. Liverpool, Liverpool L69 7ZD, UK

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First published: 22 May 2010

Abstract

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ChemInform Abstract

N-Alkyl hydroxylamines are shown to undergo a highly stereoselective cis addition to α,β-unsaturated sulfones, nitriles, and nitro compounds. The synthetic potential of this addition reaction is demonstrated for the conversion of (III) to trans-cyclohexane-1,2-diamine (IV).

chemical structure image

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