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Issue 9, 2001
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Unusual steric effects in sulfonyl transfer reactions

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Abstract

The hydrolysis of N-acyl-β-sultams generally occurs with ring opening and S–N fission in contrast to the C–N fission observed in analogous acyclic N-acyl sulfonamides. Similar to other β-sultams, the N-acyl derivatives are at least 106 more reactive than N-acylsulfonamides. However, the α-substituted 4-isopropylidene β-sultam is relatively unreactive and undergoes alkaline hydrolysis with C–N fission leaving the strained 4-membered β-sultam ring intact. This reduction in reactivity is shown to be due to steric strain introduced in the transition state for attack at the sulfonyl centre. (Z)-4-Ethylidene-β-sultam shows similar behaviour with preferential C–N fission whereas the (E)-4-ethylidene isomer and 4-isopropyl-β-sultam revert to hydrolytic ring opening with S–N fission.

Graphical abstract: Unusual steric effects in sulfonyl transfer reactions

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Article information


Submitted
05 Jun 2001
Accepted
18 Jul 2001
First published
02 Aug 2001

J. Chem. Soc., Perkin Trans. 2, 2001, 1503-1505
Article type
Paper

Unusual steric effects in sulfonyl transfer reactions

P. S. Hinchliffe, J. M. Wood, A. M. Davis, R. P. Austin, R. P. Beckett and M. I. Page, J. Chem. Soc., Perkin Trans. 2, 2001, 1503 DOI: 10.1039/B104923M

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