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Synthesis of 1,3-diaryl-3-trifluoromethylcyclopropenes by transition-metal-free reaction of 2,2,2-trifluoroacetophenone tosylhydrazones with alkynes: the effect of the trifluoromethyl group.

Authors :
Barroso R
Jiménez A
Pérez-Aguilar MC
Cabal MP
Valdés C
Source :
Chemical communications (Cambridge, England) [Chem Commun (Camb)] 2016 Mar 04; Vol. 52 (18), pp. 3677-80.
Publication Year :
2016

Abstract

1,3-Diaryl-3-trifluoromethylcyclopropenes and 2-aryl- or 2-alkyl-1,3-diaryl-3-trifluoromethylcyclopropenes are prepared in a very simple way by reaction between 1,1,1-trifluoroacetophenone tosylhydrazones and terminal or internal alkynes, respectively, in a base promoted process that does not require the presence of any metal catalyst. The essential role of the trifluoromethyl group, which enables the formation of the cyclopropenes instead of the expected pyrazoles, has been computationally investigated, suggesting the participation of a free carbene.

Details

Language :
English
ISSN :
1364-548X
Volume :
52
Issue :
18
Database :
MEDLINE
Journal :
Chemical communications (Cambridge, England)
Publication Type :
Academic Journal
Accession number :
26856259
Full Text :
https://doi.org/10.1039/c5cc10472f