Issue 24, 2004

Tandem Michael addition–carbeneinsertion reaction of 1-alkynyl(aryl)(tetrafluoroborato)-λ3-bromanes: 1-(phenylsulfonyl)- and 1-(trifluoromethylsulfonyl)cyclopentene annulation

Abstract

Exposure of 1-alkynyl[p-(trifluoromethyl)phenyl](tetrafluoroborato)-λ3-bromanes to sodium benzenesulfinate or sodium trifluoromethanesulfinate in dichloromethane at 0 °C under argon resulted in tandem Michael–carbene insertion reactions to produce 1-sulfonylcyclopentenes selectively, with concomitant formation of a small amount of rearranged 1-alkynyl sulfones.

Graphical abstract: Tandem Michael addition–carbene insertion reaction of 1-alkynyl(aryl)(tetrafluoroborato)-λ3-bromanes: 1-(phenylsulfonyl)- and 1-(trifluoromethylsulfonyl)cyclopentene annulation

Article information

Article type
Communication
Submitted
19 Jul 2004
Accepted
17 Aug 2004
First published
27 Sep 2004

Chem. Commun., 2004, 2894-2895

Tandem Michael additioncarbene insertion reaction of 1-alkynyl(aryl)(tetrafluoroborato)-λ3-bromanes: 1-(phenylsulfonyl)- and 1-(trifluoromethylsulfonyl)cyclopentene annulation

M. Ochiai, N. Tada, Y. Nishi and K. Murai, Chem. Commun., 2004, 2894 DOI: 10.1039/B410830B

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