Hydrolysis of a sulfonamide by a novel elimination mechanism generated by carbanion formation in the leaving group

J. Matthew Wood; Paul S. Hinchliffe; Andy M. Davis; Rupert P. Austin; Michael I. Page

doi:10.1039/b111340m

Hydrolysis of a sulfonamide by a novel elimination mechanism generated by carbanion formation in the leaving group

J. Matthew Wood, Paul S. Hinchliffe, Andy M. Davis, Rupert P. Austin, Michael I. Page

School of Applied Sciences

AstraZeneca

Research output: Contribution to journal › Article › peer-review

18 Citations (Scopus)

Abstract

The alkaline hydrolysis of N-α-methoxycarbonyl benzyl-β-sultam occurs 10³ times faster than the corresponding carboxylate and with rapid D-exchange at the α-carbon: the pH rate profile indicates pre-equilibirum CH ionisation and together with formation of benzoyl formate as a product this suggests a novel mechanism for hydrolysis.

Original language	English
Pages (from-to)	772-773
Number of pages	2
Journal	Chemical Communications
Issue number	7
Early online date	12 Mar 2002
DOIs	https://doi.org/10.1039/b111340m
Publication status	Published - 7 Apr 2002

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title = "Hydrolysis of a sulfonamide by a novel elimination mechanism generated by carbanion formation in the leaving group",

abstract = "The alkaline hydrolysis of N-α-methoxycarbonyl benzyl-β-sultam occurs 103 times faster than the corresponding carboxylate and with rapid D-exchange at the α-carbon: the pH rate profile indicates pre-equilibirum CH ionisation and together with formation of benzoyl formate as a product this suggests a novel mechanism for hydrolysis.",

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doi = "10.1039/b111340m",

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journal = "Chemical Communications",

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AU - Wood, J. Matthew

AU - Hinchliffe, Paul S.

AU - Davis, Andy M.

AU - Austin, Rupert P.

AU - Page, Michael I.

PY - 2002/4/7

Y1 - 2002/4/7

N2 - The alkaline hydrolysis of N-α-methoxycarbonyl benzyl-β-sultam occurs 103 times faster than the corresponding carboxylate and with rapid D-exchange at the α-carbon: the pH rate profile indicates pre-equilibirum CH ionisation and together with formation of benzoyl formate as a product this suggests a novel mechanism for hydrolysis.

AB - The alkaline hydrolysis of N-α-methoxycarbonyl benzyl-β-sultam occurs 103 times faster than the corresponding carboxylate and with rapid D-exchange at the α-carbon: the pH rate profile indicates pre-equilibirum CH ionisation and together with formation of benzoyl formate as a product this suggests a novel mechanism for hydrolysis.

UR - https://www.scopus.com/pages/publications/0037035325

U2 - 10.1039/b111340m

DO - 10.1039/b111340m

M3 - Article

AN - SCOPUS:0037035325

SN - 1359-7345

SP - 772

EP - 773

JO - Chemical Communications

JF - Chemical Communications

IS - 7

ER -

Hydrolysis of a sulfonamide by a novel elimination mechanism generated by carbanion formation in the leaving group

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