Leaving group effects in reductively triggered fragmentation of 4-nitrobenzyl carbamates

…, D Bohinc-Herceg, NA Helsby, CJ O'Connor…

Index: Sykes, Bridget M.; Hay, Michael P.; Bohinc-Herceg, Dubravka; Helsby, Nuala A.; O'Connor, Charmian J.; Denny, William A. Journal of the Chemical Society, Perkin Transactions 1, 2000 , # 10 p. 1601 - 1608

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Citation Number: 21

Abstract

The rates and extent of release of a series of substituted anilines from 4-nitrobenzyl carbamates, following nitro group reduction by radiolytic, enzymic and chemical methods, are reported. The yield of released anilines decreased over the pH range 4–7, but was independent of the basicity of the leaving aniline. Detailed studies of the fragmentation of one example identified the 4-hydroxylamine as the key intermediate. At pH greater than 5 ...