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.
F. Benfatti; G. Cardillo; L. Gentilucci; R. Perciaccante; A. Tolomelli
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11585/19419
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