The reaction of alpha-bromo-beta,gamma-unsaturated lactams and esters with m-chloroperbenzoic acid has been studied to find experimental conditions that could afford exclusively epoxide formation or bromide 1,3-shift. The results show a strong dependence of reactivity on the dilution and on the amount of peracid used, suggesting a radical mechanism for the bromine rearrangement. This last reaction is also strongly favored by microwave assisted conditions.
F. Benfatti, G. Cardillo, L. Gentilucci, R. Perciaccante, A. Tolomelli (2005). An investigation of the reactivity of MCPBA and alpha-bromoalkenes under traditional or microwave-assisted conditions: Selective formation of epoxides or allylic bromides. SYNLETT, 14, 2204-2208 [10.1055/s-2005-872254].
An investigation of the reactivity of MCPBA and alpha-bromoalkenes under traditional or microwave-assisted conditions: Selective formation of epoxides or allylic bromides.
BENFATTI, FIDES;CARDILLO, GIULIANA;GENTILUCCI, LUCA;PERCIACCANTE, ROSSANA;TOLOMELLI, ALESSANDRA
2005
Abstract
The reaction of alpha-bromo-beta,gamma-unsaturated lactams and esters with m-chloroperbenzoic acid has been studied to find experimental conditions that could afford exclusively epoxide formation or bromide 1,3-shift. The results show a strong dependence of reactivity on the dilution and on the amount of peracid used, suggesting a radical mechanism for the bromine rearrangement. This last reaction is also strongly favored by microwave assisted conditions.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
