Molecular mechanism of Diels–Alder reaction between (E)-3,3,3-trichloro-1-nitropropene and cyclopentadiene: B3LYP/6-31G(d) computational study

Authors : Radomir JASINSKI, Andrzej BARANSKI

Pages : 848-852

Doi:10.3906/kim-1208-13

View : 16 | Download : 9

Publication Date : 0000-00-00

Article Type : Research Paper

Abstract :Analysis of reactivity indexes supports the polar character of the reaction between insert ignore into journalissuearticles values(E);-3,3,3-trichloro-1-nitropropene and cyclopentadiene. This is confirmed by the analysis of electronic properties of transition complexes involved in the reaction paths using the B3LYP/6-31Ginsert ignore into journalissuearticles values(d); algorithm. The transition state`s asymmetry is large, but it is insufficient to provoke a zwitterionic reaction mechanism. Attempts to find a heterocyclic intermediate 7 in the reaction path ultimately leading to 5-endo-nitro-6-exo-trichloromethylnorbornene 3 have been unsuccessful.
Keywords : Polar Diels Alder reaction, mechanism, cyclopentadiene, nitroalkene, electrophilicity, nucleophilicity