X-ray crystallographic investigation of the adduct of 1-demethylamino-2-(4-bromophenyl-2H-isoindole with N-phenylmalemide

✍ Scribed by T. T. Kucherenko; P. V. Muzyka; É. B. Rusanov; A. N. Chernega; V. A. Kovtunenko; A. K. Tyltin; F. S. Babichev

• Book ID: 104781832
• Publisher: Springer US
• Year: 1992
• Tongue: English
• Weight: 258 KB
• Volume: 28
• Category: Article
• ISSN: 0009-3122
• DOI: 10.1007/bf00475247

✦ Synopsis

An unusual path for the reaction of 2-aryl-l-dimethylamino-2H-isoindoles with N-R-maleimMes, leading to the imides of 1,2-dihydronaphthalene-2,3-dicarboxylic acids, was established by x-ray co, stallographic analysis.

1-Dimethylamino-2-arylisoindoles (I) were described in 1971 [1]. Our interest in the addition of maleimide derivatives to these compounds has not diminished since that time [2][3][4]. This interest is governed by an endeavor to find the fullest correlation between the various spectral characteristics of the obtained adducts and their structures. In the first investigation [2] the ease of cycloaddition was demonstrated, and the exo structure (III) was assigned to the products from the reaction of compounds (I) with (II) on the basis of the PMR spectra. In this paper questions arose in connection with the anomalously high value of the spin--spin coupling constant 3J56 of 13.5 Hz for this structure, and this was subsequently explained by means of a wide range of subjects [3] as resulting from transoid fusion of the rings in the adduct (IV), where the 5-H and 6-H protons lie at an angle of 156-158 ~ in relation to the C--C bond.