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.
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.File in questo prodotto:
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