Journal of Organic Chemistry p. 2680 - 2684 (1987)
Update date:2022-08-05
Topics:
Mahaffy, P. G.
Visser, D.
Torres, M.
Bourdelande, J. L.
Strausz, O. P.
The gas-phase photolyses of hexafluoro-3-diazo-2-butanone (1), octafluoro-2-diazo-3-pentanone (2), and octafluoro-3-diazo-2-pentanone (3) have been studied.Chemical trapping experiments with hexafluoro-2-butyne provide evidence that isomeric ketocarbene intermediates equilibrate, presumably via transient 4-?-electron oxirenes. 1 yields tetrakis(trifluoromethyl)furan (8) as a major product, with a trace of 1,2,3-tris(trifluoromethyl)-3-(trifluoroacetyl)cyclopropene (9) and bis(trifluoromethyl)ketene (10).Photolysis of either 2 or 3 yields the same four trapped products: 2-(pentafluoroethyl)-3,4,5-tris(trifluoromethyl)furan (12), 3-(pentafluoroethyl)-2,4,5-tris(trifluoromethyl)furan (14), 1,2,3-tris(trifluoromethyl)-3-(pentafluoropropionyl)cyclopropene (13), and 1,2-bis(trifluoromethyl)-3-(pentafluoroethyl)-3-(trifluoroacetyl)cyclopropene (15), in approximately the same ratio, along with the Wolff rearrangement product, (pentafluoroethyl)(trifluoromethyl)ketene (16).
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