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Molecules 2013, 18(4), 4293-4307; doi:10.3390/molecules18044293

Manganese(III) Acetate-mediated Oxidative Cyclization of a-Methylstyrene and trans-Stilbene with b-Ketosulfones

Laboratoire de Pharmaco-Chimie Radicalaire, Faculté de Pharmacie, Aix-Marseille Univ, CNRS, Institut de Chimie Radicalaire ICR, UMR 7273, 27 Bd Jean Moulin, CS 30064, 13385 Marseille Cedex 05, France
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Author to whom correspondence should be addressed.
Received: 27 February 2013 / Revised: 3 April 2013 / Accepted: 4 April 2013 / Published: 11 April 2013
(This article belongs to the Section Organic Synthesis)
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Abstract

A convenient microwave irradiation protocol was utilized for the synthesis of b-ketosulfones 15 in good yields. These sulfones reacted with alkenes through a radical oxidative cyclization mediated by Mn(OAc)3. Dihydrofurans 610 were obtained in moderate to good yields starting from 1,1-disubstituted alkenes. Dihydrofurans 1115 were synthesized in moderate yields and unexpected cyclopropanes 1619 were obtained in low yields starting from 1,2-disubstituted alkenes. This protocol offers access to various dihydrofurans which could be tested for their antiparasitic potential. View Full-Text
Keywords: manganese(III) acetate; dihydrofuran; radicals manganese(III) acetate; dihydrofuran; radicals
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Bouhlel, A.; Curti, C.; Tabelé, C.; Vanelle, P. Manganese(III) Acetate-mediated Oxidative Cyclization of a-Methylstyrene and trans-Stilbene with b-Ketosulfones. Molecules 2013, 18, 4293-4307.

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