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Regioselective free radical phenylsulfenation of a non-activated delta-carbon atom by the photolysis of alkyl benzenesulfenate

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2003
Authors
Petrović, G
Saičić, Radomir
Čeković, Živorad
Article (Published version)
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Abstract
A regioselective free radical introduction of a phenylthio group onto a non-activated delta-carbon atom was achieved by photolysis of alkyl benzenesulfenates in the presence of hexabutylditin, and delta-phenylthio alcohols were obtained in 35-91% yields. delta-Phenylsulfenylation of a non-activated carbon atom induced only by irradiation of alkyl benzenesulfenates (without initiation by hexabutylditin) also occurs, however, slower reaction rates were observed and lower yields of delta-phenylthio alcohols were obtained. (C) 2002 Published by Elsevier Science Ltd.
Keywords:
radicals and radical reactions / 1,5-hydrogen migration / intramolecular fuctionalization / sulfenic acids and derivatives / sulfides / delta-phenylthio alcohols
Source:
Tetrahedron, 2003, 59, 2, 187-196
Publisher:
  • Pergamon-Elsevier Science Ltd, Oxford

DOI: 10.1016/S0040-4020(02)01477-1

ISSN: 0040-4020

WoS: 000180259400007

Scopus: 2-s2.0-0037421130
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URI
http://cherry.chem.bg.ac.rs/handle/123456789/532
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