Dimerization and cycloaddition reactions of a trimethylenemethane derivative, 2-isopropylidenecyclopenta-1, 3-diyl. Mechanistic separation of triplet and singlet …

LR Corwin, DM McDaniel, RJ Bushby…

Index: Corwin, Leonard R.; McDaniel, Dale M.; Bushby, Richard J.; Berson, Jerome A. Journal of the American Chemical Society, 1980 , vol. 102, # 1 p. 276 - 287

Full Text: HTML

Citation Number: 28

Abstract

Abstract: Pyrolysis of 7-isopropqlidene-2, 3-diazanorbornene (1) at 60" C in solution liberates N2 and 2-isopropylidenecyclopenta-1, 3-diyl (2). The diyl (2) dimerizes readily, but, in the presence of an olefinic trapping agent, 2 can be intercepted as either a fused adduct, F, a bicyclo [3.3. 0] oct-l-ene, or a bridged adduct, B, a 7-isopropylidenenorbornane. The composition of the adduct mixture is dependent on the initial concentration of the trapping ...