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

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

文献索引：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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被引用次数: 21

摘要

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 ...