Issue 5, 2010
From the journal:

Chemical Communications

Novel dienone-phenol type rearrangement of 4,4-disubstituted cyclohexadienone system using thiosilane†

Yasufumi Wada,‡a   Kouji Otani,a   Noriko Endo,a   Yasuyuki Kita§a  and  Hiromichi Fujioka*a  

* Corresponding authors

a Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamada-oka, Suita, Osaka, Japan
E-mail: fujioka@phs.osaka-u.ac.jp
Fax: +81 6 6879 8229
Tel: +81 6 6879 8225

Abstract

Thiosilane and a catalytic amount of a Brønsted acid mediate the novel domino-type rearrangement reaction of the 4,4-disubstituted cyclohexadienones to produce the 3,4-disubstituted benzenethioethers; the key step is 1,2-addition of thiosilane to dienone.

Graphical abstract: Novel dienone-phenol type rearrangement of 4,4-disubstituted cyclohexadienone system using thiosilane

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Article information

DOI
https://doi.org/10.1039/B915294F
Article type
Communication
Submitted
28 Jul 2009
Accepted
17 Nov 2009
First published
09 Dec 2009

Chem. Commun., 2010,46, 797-799

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Novel dienone-phenol type rearrangement of 4,4-disubstituted cyclohexadienone system using thiosilane

Y. Wada, K. Otani, N. Endo, Y. Kita and H. Fujioka, Chem. Commun., 2010, 46, 797 DOI: 10.1039/B915294F

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