alpha-Oxothiones, part IV - Electrophilic substitution of phenols with alpha,alpha '-dioxothiones and ortho-thioquinones

Authors
Capozzi, G Menichetti, S Nativi, C
Citation
G. Capozzi et al., alpha-Oxothiones, part IV - Electrophilic substitution of phenols with alpha,alpha '-dioxothiones and ortho-thioquinones, EUR J ORG C, (21), 2000, pp. 3653-3657
Citations number
22
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
1434193X → ACNP
Issue
21
Year of publication
2000
Pages
3653 - 3657
Database
ISI
SICI code
1434-193X(200011):21<3653:API-ES>2.0.ZU;2-Z
Abstract
alpha,alpha'-Dioxothione 1a and ortho-thioquinones 2a and 2b are able to re act with several phenols and N,N-dimethylaniline to give the corresponding alkyl aryl or diaryl sulfides. The mechanism of this reaction was proved to be an electrophilic aromatic substitution undergone by the highly polarise d carbon-sulfur double bond. Following this procedure, the atropoisomeric b iphenyl compound 26 was also prepared.