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The alkaline hydrolysis of sulfonate esters: challenges in interpreting experimental and theoretical data

Abstract:

Sulfonate ester hydrolysis has been the subject of recent debate, with experimental evidence interpreted in terms of both stepwise and concerted mechanisms. In particular, a recent study of the alkaline hydrolysis of a series of benzene arylsulfonates (Babtie et al., Org. Biomol. Chem.10, 2012, 8095) presented a nonlinear Brønsted plot, which was explained in terms of a change from a stepwise mechanism involving a pentavalent intermediate for poorer leaving groups to a fully concerted mechani...

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Publication status:
Published
Peer review status:
Peer reviewed

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Publisher copy:
10.1021/jo402420t

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Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Role:
Author
Publisher:
American Chemical Society
Journal:
Journal of Organic Chemistry More from this journal
Volume:
79
Issue:
7
Pages:
2816-2828
Publication date:
2013-11-26
DOI:
EISSN:
1520-6904
ISSN:
0022-3263
Language:
English
Pubs id:
1170222
Local pid:
pubs:1170222
Deposit date:
2021-04-02

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