CYCLOADDITION OF [3]DENDRALENE DERIVATIVES TO DINITROBENZOFUROXAN AND NITROBENZODIFUROXAN
DOI:
https://doi.org/10.1007/2710Keywords:
dendralene, dinitrobenzofuroxan, nitrobenzodifuroxan, cascade cycloaddition, Diels–Alder reactionAbstract
It has been shown experimentally (by NMR spectroscopy and X-ray structural analysis) and theoretically (by quantum-chemical calculations according to DFT with B3LYP/6-31G* basis set) that the cycloaddition of [3]dendralene derivatives to nitrobenzodifuroxan and dinitrobenzofuroxan occurs by a stepwise mechanism with a σ-complex as intermediate. It was shown that the cycloaddition steps occurring contrary to the Alder endo rule are characterized by significant global electrophilicity index differences for the reagents (Δω > 3.0 eV). The stages with Δω ≤ 3.0 eV occurred in accordance with the Alder endo rule as concerted processes. X-ray structural analysis and quantum-chemical calculations within the framework of AIM model identified intramolecular attraction forces between non-bonded atoms in the cycloadduct of phenyldendralene and nitrobenzodifuroxan.
How to Cite
Morozov, P. G.; Kurbatov, S. V.; Semenyuk, Yu. P.; Burov, O. N.; Kletskii, M. E.; Fedik, N. S.; Suzdalev, K. F. Chem. Heterocycl. Compd. 2015, 51, 903. [Khim. Geterotsikl. Soedin. 2015, 51, 903.]
For this article in the English edition see DOI 10.1007/s10593-015-1794-2
