Journal of Organic Chemistry p. 2168 - 2172 (1986)
Update date:2022-09-26
Topics:
Moss, Robert A.
Kmiecik-Lawrynowicz, Grazyna
Krogh-Jespersen, Karsten
Fluorophenoxycarbene (FCOPh) was generated by thermolysis (50 deg C) of 3-fluoro-3-phenoxydiazirine and added to six alkenes, affording the corresponding cyclopropanes.The substrates and relative reactivities were the following: tetramethylethylene (7.14), trimethylethylene (17.9), isobutene (14.3), 1-hexene (1.00), methyl acrylate (18.7), and acrylonitrile (33.6).The ambiphilic reactivity pattern of FCOPh resembles those of ClCOPh and ClCOMe.An ab anitio study of FCOPh afforded geometries and frontier orbital energies of the cis and trans conformers of the carbene.Both conformers are predicted to be ambiphiles in alkene addition reactions, on the basis of simple frontier molecular orbital considerations
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