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CYCLOADDITION OF [3]DENDRALENE DERIVATIVES TO DINITROBENZOFUROXAN AND NITROBENZODIFUROXAN

Павел Г. Морозов, Сергей В. Курбатов, Юлия П. Семенюк, Олег Н. Буров, Михаил Е. Клецкий, Никита С. Федик, Константин Ф. Суздалев
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Abstract


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

 


Keywords


dendralene; dinitrobenzofuroxan; nitrobenzodifuroxan; cascade cycloaddition; Diels–Alder reaction

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