Koichi Komatsu, Masami Fujimori, Kunio Okamoto
1977
Citations
0
Influential Citations
27
Citations
Journal
Tetrahedron
Abstract
Abstract 8 Phenyl- ( 2 ) and 8,8 diphenyl-heptafulvenes ( 3 ) have been synthesized and fully characterized. The 220 MHz NMR data on 2 and 3 , as well as the 13C NMR data on 3 , indicates only a small contribution of the dipolar structure for this system. The electrophilic and nucleophilic reagents react at different sites of this system while protonation of 2 and 3 occurs at the exocyclic methylene carbon butylation occurs at the 7 -membered ring, i.e. the 1- and 3-positions of 2 and only at the 3-position of 3 , when treated with n-BuLi. Cycloaddition with tetracyanoethylene gives the [8 + 2]-cycloadduct for 2 and the [4 + 2] adduct for 3 .