Remarkable efficiency of the aryne chemistry of (dehydro)octafluoro[2.2]paracyclophane when using the Cadogan method.
Generation of the aryne, (dehydro)octafluoro[2.2]paracyclophane, from its acetamide derivative utilizing the Cadogan method led to remarkable results with respect to Diels-Alder and ene reactivity. A comparison was made between this new and virtually unused method and our earlier reported results using Cram methodology (reaction of aryl iodide with potassium tert-butoxide). Surprisingly, no ene reactivity was observed with the Cram methodology. This mechanistic conundrum was examined extensively with no unambiguous explanation for the difference in reactivity being found.
Dolbier
William R
WR
Department of Chemistry, University of Florida, P.O. Box 117200, Gainesville, Florida 32611-7200, USA. wrd@chem.ufl.edu
Zhai
Yi-An
YA
Wheelus
Will
W
Battiste
Merle A
MA
Ghiviriga
Ion
I
Bartberger
Michael D
MD