Manganese(III) acetate-mediated oxidative cyclization of a-methylstyrene and trans-stilbene with b-ketosulfones

A convenient microwave irradiation protocol was utilized for the synthesis of b-ketosulfones 1-5 in good yields. These sulfones reacted with alkenes through a radical oxidative cyclization mediated by Mn(OAc)3. Dihydrofurans 6-10 were obtained in moderate to good yields starting from 1,1-disubstitut...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2013-04, Vol.18 (4), p.4293-4307
Main Authors: Bouhlel, Ahlem, Curti, Christophe, Tabelé, Clémence, Vanelle, Patrice
Format: Article
Language:English
Subjects:
Acetates - chemistry
Alkenes - chemistry
Antiparasitic Agents - chemical synthesis
Antiparasitic Agents - chemistry
Carbon
Cyclization
Cyclopropanes - chemical synthesis
dihydrofuran
Furans - chemical synthesis
Furans - chemistry
Hydrocarbons
manganese(III) acetate
Microwaves
Organometallic Compounds - chemistry
Oxidation-Reduction
radicals
Stilbenes - chemistry
Styrenes - chemistry
X-Rays
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Summary:A convenient microwave irradiation protocol was utilized for the synthesis of b-ketosulfones 1-5 in good yields. These sulfones reacted with alkenes through a radical oxidative cyclization mediated by Mn(OAc)3. Dihydrofurans 6-10 were obtained in moderate to good yields starting from 1,1-disubstituted alkenes. Dihydrofurans 11-15 were synthesized in moderate yields and unexpected cyclopropanes 16-19 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.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules18044293