Regioselectivity of Arylation of 2,3’-Biquinolyl Dianion 英文参考文献.docVIP

Molecules 1999, 4, 126-134 molecules ISSN 1420-3049 Regioselectivity of Arylation of 2,3’-Biquinolyl Dianion A.V. Aksenov *, I.V. Aksenova , I.V. Borovlev and Yu. I. Smushkevich 1 1 1 2 1 Stavropol State University, Chair of Organic Chemistry, 1 Pushkina str, 355009 Stavropol, Russia Fax 007 (8652) 354033, E-mail: stavsu@stavsu.ru Russian Mendeleev University of Chemical Technology, Chair of Organic Chemistry, 9 Miusskaya sq., 2 125047 Moscow, Russia *Author to whom correspondence should be addressed. Received: 27 January 1998 / Accepted: 8 March 1999 / Published: 26 April 1999 Abstract: The dianion of 2,3’-biquinolyl with aryl- and hetaryl halides forms the products of arylation to 4’-position, which on treatment with alkyl halides or water yield 1’-alkyl- 1’,4’dihydro-2,3’-biquinolyls or 4’-aryl-1’,4’-dihydro-2,3’-biquinolyls respectively. The oxidation of the latter leads to 4’-aryl-2,3’-biquinolyls. The cation dependence of the arylation is shown. Keywords: Regioselectivity, 2,3’-biquinolyl dianion. Introduction Recently [1] we have developed a procedure for the generation of the 2,3’-biquinolyl dianion (1) which has enabled us to study its properties. The present work is devoted to its arylation and heteroarylation. The studied reactions of such species with aryl halides include, as a rule, the transfer of electrons from the dianion (anion-radical) to the halogenated derivative [2-4]. Thus the dianion of biphenyl reacts with halobenzenes yielding benzoic acid after treatment of the reaction mixture with carbon dioxide [2]. We supposed that the dianion 1 would also behave as an electron donor respective to aryl halides. However, we supposed that due to the greater affinity of 1 to electrons compared to that of biphenyl