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Structure of the Cycloaddition Products of Pyrido[2,1‐ a ]isoindole with Maleimide Derivatives: X‐ray Diffraction Analysis and 1 H NMR Variable‐Temperature Spectra
Author(s) -
Voitenko Zoia V.,
Pocholenko Olexander A.,
Chkarov Oleg O.,
Shishkin Oleg V.,
Shishkina Svetlana V.,
Dall’Ava Alain,
Vedrenne Marc,
Sanchez Michel,
Wolf JeanGérard
Publication year - 2001
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200104)2001:7<1401::aid-ejoc1401>3.0.co;2-m
Subject(s) - isoindole , maleimide , chemistry , atropisomer , cycloaddition , diffraction , crystallography , cope rearrangement , x ray crystallography , stereochemistry , polymer chemistry , organic chemistry , catalysis , physics , optics
Investigation of the cycloaddition reaction under thermodynamic control of pyrido[2,1‐ a ]isoindole with maleimide derivatives revealed a new rearrangement leading to 2‐{2′‐[(1 R )2,5‐dioxopyrrolidinylidene]‐2′‐[(1 R )‐2,5‐dioxopyrrolidinyl)methyl]}phenylpyridine. Their structure was confirmed by X‐ray diffraction analysis. The atropisomeric properties of the obtained compounds were examined in a detailed NMR spectroscopic study. Dependence of the spectra on temperature was investigated, and coalescence temperatures and conversion barriers between the corresponding atropisomers determined.