Acyl vs sulfonyl transfer in N-acyl β-sultams and 3-oxo-β-sultams

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Page, Michael I. (2003) Acyl vs sulfonyl transfer in N-acyl β-sultams and 3-oxo-β-sultams. Organic Letters, 6 (2). pp. 201-203. ISSN 1523-7060

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Official URL: http://pubs.acs.org/cgi-bin/abstract.cgi/orlef7/20...

DOI: 10.1021/ol0361305

Abstract

N-Acylsulfonamides usually react with nucleophiles by acyl transfer and C-N bond fission. However, the hydrolysis of N-acyl -sultams is a sulfonyl transfer reaction that occurs with S-N fission and opening of the four-membered ring. Similar to other -sultams, the N-acyl derivatives are at least 106-fold more reactive than N-acyl sulfonamides. 3-Oxo--sultams are both -lactams and -sultams but also hydrolyze with preferential S-N bond fission.

Item Type:	Article
Subjects:	Q Science > Q Science (General) Q Science > QD Chemistry
Schools:	School of Applied Sciences School of Applied Sciences > Biomolecular Sciences Research Centre
Related URLs:	Author
Depositing User:	Sara Taylor
Date Deposited:	08 Feb 2008 13:03
Last Modified:	19 Jan 2010 04:48
URI:	http://eprints.hud.ac.uk/id/eprint/516

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