Ai. Vokin et al., Spectral monitoring of tricyanovinylation of 2-phenylpyrrole and 4,5,6,7-tetrahydroindole. Self-association of the final products, RUSS J ORG, 36(10), 2000, pp. 1504-1508
Pyrroles readily and selectively react with tetracyanoethylene in DMSO yiel
ding the corresponding 2-tricyanovinyl derivatives. The reaction involves i
ntermediate formation of donor-acceptor pi,pi*-complex. 2-Phenyl-5-(1,2,2-t
ricyanovinyl)pyrrole exists in saturated hydrocarbons as sandwich-like inte
rmolecular associates; in the crystalline state, complexes with hydrogen bo
nd are also formed. According to the ESR data, tricyanovinylpyrroles in cry
stal give rise to radical anions via electron transfer between the componen
ts of self-associates.