280747-80-0Relevant academic research and scientific papers
Mechanism of hydrogen atom transfer in the photolytic rearrangement of N-bromophenylalaninamide derivatives
Easton, Christopher J.,Merrett, Martin C.,Razzino, Pasquale
, p. 693 - 697 (2007/10/03)
Photolysis of N-bromo-N-tert-butyl-Na-phthaloylphenylalaninamide gave a 1:1 mixture of the diastereomers of 3-bromo-N-tert-butyl-Na-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, indicating that the bromophenylalanine derivatives are formed through an intermolecular process and not by intramolecular 1,4-hydrogen atom transfer of the corresponding amidyl radical. Results of reactions of N-bromo-N-tert-butyl-Na-phthaloyl-p-methylphenylalaninamide are also consistent with this interpretation. Reactions of stereoselectively β-deuteriated derivatives of N-bromo-N-tert-butyl-Na-phthaloylphenylalaninamide established that the pro-S benzylic hydrogen of the phenylalaninamide is selectively abstracted, by a factor of ca. 3.8, in this intermolecular process.
Regioselective Functionalization of N-Phthaloyl-Substituted Amino Acid and Peptide Derivatives
Easton, Christopher J.,Hutton, Craig A.,Rositano, Giovanna,Tan, Eng Wui
, p. 5614 - 5618 (2007/10/02)
The free-radical reactions of a range of amino acid derivatives with N-bromosuccinimide are described.The products and relative rates of these reactions indicate that the α-position of an N-phthaloyl-substituted α-amino acid derivative is much less reacti
