The rotameric (R,S)- and (R,R)-biaryl-3,3′-diphthalides of polyphenylene series

被引：8

作者：

Yangirov, Tagir A. ^{[1
]}

Fatykhov, Akhnef A. ^{[1
]}

Sedova, Elvira A. ^{[1
]}

Khalilov, Leonard M. ^{[2
]}

Meshcheryakova, Ekaterina S. ^{[2
]}

Ivanov, Sergey P. ^{[1
]}

Salazkin, Sergey N. ^{[3
]}

Kraikin, Vladimir A. ^{[1
]}

机构：

[1] Russian Acad Sci UIC UFRC RAS, Ufa Inst Chem, Ufa Fed Res Ctr, Prospekt Oktyabrya 69, Ufa 450054, Russia

[2] Inst Petrochem & Catalysis UFRC RAS, Ufa, Russia

[3] Russian Acad Sci, AN Nesmeyanov Inst Organoelement Cpds, Moscow, Russia

来源：

TETRAHEDRON | 2019年 / 75卷 / 09期

关键词：

Biaryl-3,3 '-diphthalides; meso- and chiral diastereomers; cis and trans rotamers; X-ray analysis; 1H and 13C NMR; LIQUID-CHROMATOGRAPHIC SEPARATION; AROMATIC POLYMERS; DIASTEREOMERIC DERIVATIVES; DIRECTED RESOLUTION; CARBOXYLIC-ACIDS; BEHAVIOR; ENANTIOMERS; ESTERS; AMIDES;

D O I：

10.1016/j.tet.2019.01.043

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A wide range of diastereomeric pairs of biaryl-3,3'-diphthalides with aromatic (heteroaromatic) substituents of polyphenylene series (including halogen substituted) was synthesized. All of them were separated and characterized by the methods of X-ray analysis, HPLC, IR-, 1H and 13C NMR spectroscopy. It was determined that solubility, tendency to adsorption and related to it retention times, chemical shifts of equivalent hydrogen and carbon atoms of biaryl-3,3'-diphthalides diastereoisomers are determined firstly by the stereo-electronic effects of two adjacent strongly polar phthalide groups. It was shown that both in crystalline phase and in solution all the diphthalides, regardless of the chemical structure of their substituents, are existing as stable rotamers with cis or synperiplanar (chiral forms) and trans or antiperiplanar (meso-forms) conformation. (C) 2019 Elsevier Ltd. All rights reserved.

引用

页码：1282 / 1292

页数：11

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The rotameric (R*,S*)- and (R*,R*)-biaryl-3,3′-diphthalides of polyphenylene series

The rotameric (R,S)- and (R,R)-biaryl-3,3′-diphthalides of polyphenylene series