20464-99-7Relevant academic research and scientific papers
Phosphoryl to carbonyl migration of amino groups in mixed anhydrides
Symes, Jill,Modro, Tomasz A.
, p. 1702 - 1708 (2007/10/02)
Mixed anhydrides derived from carboxylic and aminophosphoric acids, (RO)(R'2N)P(O)OC(O)R'' (1), undergo unimolecular fragmentation yielding carboxyamides, R''C(O)NR'2, and metaphosphate esters, ROPO2.The mechanism of the amino group transfer was studied for substrate 1a (1, R = R' = Me; R'' = Ph); solvent as well as substituent effects indicate little (if any) charge development in the transition state.The effects of solvents and Lewis acids on the reaction rate and the activation parameters determined for 1a can be explained best in terms of stabilizing interactions with either carboxyamide or metaphosphate being formed in the course of reaction.The transfer of a functional group from one acyl center to another was investigated for other anhydride systems and the relative contributions of the fragmentation vs. disproportionation of substrates are discussed.
Phosphoric Amides. 7 - Mass Spectrometry of Phosphoric Amido Esters: Fragmentation Patterns and Migratory Aptitudes
Dawidowitz, Bette,Modro, Tomasz A.
, p. 128 - 134 (2007/10/02)
Mass spectra of 38 organophosphorus compounds, containing both phosphate ester (P(O)OR) and phosphoramidate (P(O)NR'R'') functional groups, were recorded and discussed.Attention was focused on P-N bond cleavage, which can involve simple fission, fission a
