Volume 33, Issue 8
Preparative Organic Chemistry
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ChemInform Abstract: The Synthesis of β-N-Tosylamino Hydroxylamines via the Ring Opening of N-Tosylaziridines and Their Use in Reverse Cope Cyclizations.

Ian A. O'Neil

Ian A. O'Neil

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

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J. Chris Woolley

J. Chris Woolley

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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Heather Hobbs

Heather Hobbs

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

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First published: 22 May 2010

Abstract

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ChemInform Abstract

Title compounds (I) are found to undergo regioselective ring opening with hydroxylamines to give β-N-tosylamino hydroxylamines. Suitable substrates, such as (VI), undergo reverse Cope cyclizations to give amino-functionalized pyrrolidine and piperidine N-oxides.

chemical structure image

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