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

DOI

10.3906/kim-1208-13

Abstract

Analysis of reactivity indexes supports the polar character of the reaction between (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/6-31G(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

First Page

848

Last Page

852

Recommended Citation

JASINSKI, RADOMIR and BARANSKI, ANDRZEJ (2013) "Molecular mechanism of Diels--Alder reaction between (E)-3,3,3-trichloro-1-nitropropene and cyclopentadiene: B3LYP/6-31G(d) computational study," Turkish Journal of Chemistry: Vol. 37: No. 5, Article 15. https://doi.org/10.3906/kim-1208-13
Available at: https://journals.tubitak.gov.tr/chem/vol37/iss5/15