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1,3‐Dipolar Cycloadditions of 1,1‐Difluoroallene, Nitrones, Nitrile‐Oxides and Carbonyl Ylides
Author(s) -
Dolbier William R.,
Burkholder Conrad R.
Publication year - 1985
Publication title -
israel journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.908
H-Index - 54
eISSN - 1869-5868
pISSN - 0021-2148
DOI - 10.1002/ijch.198500080
Subject(s) - chemistry , regioselectivity , nitrile , ylide , dipole , oxide , nitrone , computational chemistry , medicinal chemistry , photochemistry , organic chemistry , cycloaddition , catalysis
The 1,3‐dipolar cycloadditions of C,N‐diphenylnitrone, C‐phenyl‐N‐methylnitrone, triphenylnitrone, mesitylnitrile oxide and tetracyanocarbonyl ylide with 1,1‐difluoroallene (DFA) are reported and discussed with respect to regiochemistry. Each of the dipoles adds exclusively to the C 2 —C 3 , non‐fluorine‐substituted π‐bond of DFA. The nitrones all undergo regiospecific reactions while mesitylnitrile oxide does not. The results are discussed with respect to FMO theory and other factors which can give rise to regiochemical variation.