Mechanism of hydrogen atom transfer in the photolytic rearrangement of N-bromophenylalaninamide derivatives

CJ Easton, MC Merrett, P Razzino

Index: Easton, Christopher J.; Merrett, Martin C.; Razzino, Pasquale Journal of the Chemical Society. Perkin Transactions 2, 2000 , # 4 p. 693 - 697

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Abstract

Photolysis of N-bromo-N-tert-butyl-N α-phthaloylphenylalaninamide gave a 1∶ 1 mixture of the diastereomers of 3-bromo-N-tert-butyl-N α-phthaloylphenylalaninamide. Reactions carried out with various concentrations of the N-bromoamide, and in the presence of 4-tert- butyltoluene, showed that the ratio of the product bromophenylalanine derivatives to 4-tert- butylbenzyl bromide varied as a function of the concentration of the N-bromoamide, ...