Synlett 2005(14): 2204-2208  
DOI: 10.1055/s-2005-872254
LETTER
© Georg Thieme Verlag Stuttgart · New York

An Investigation of the Reactivity of MCPBA and α-Bromoalkenes under ­Traditional or Microwave-Assisted Conditions: Selective Formation of ­Epoxides or Allylic Bromides

Fides Benfatti, Giuliana Cardillo*, Luca Gentilucci, Rossana Perciaccante, Alessandra Tolomelli
Department of Chemistry ‘G. Ciamician’, University of Bologna, Via Selmi 2, 40126 Bologna, Italy
Fax: +39(051)2099456; e-Mail: giuliana.cardillo@unibo.it;
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Publication History

Received 15 June 2005
Publication Date:
29 July 2005 (online)

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Abstract

The reaction of α-bromo-β,γ-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.