New Selective Approach To p-Chlorocalix{[}4]arenes Synthesis / Mitin Viktor V.,Ivanova Ekaterina A.,Prokhorova Polina E.,Morzherin Yury Yu // LETTERS IN ORGANIC CHEMISTRY. - 2016. - V. 13, l. 9. - P. 625-628.

ISSN/EISSN:

1570-1786 / 1875-6255

Type:

Article

Abstract:

Background: Calixarenes are well-known building blocks in supramolecular chemistry. Introduction of the halogen atom at the upper rim of the molecule allows to obtain very promising synthons for synthesis of more complex calixarene structures. Each halogen is specific for the certain types of reactions. It is known that chlorine derivatives are preferable for the Kumada, Hiyama, Stille, Negishi, Suzuki cross-coupling reaction and Buchwald-Hartwig amination. para-Chlorinated derivatives of calix{[}4]arene were described in the literature even less than other halogenated ones because of their synthesis complication (low yield construction from chlorophenols). Methods: To increase the yield of p-chlorinated calix{[}4]arene and to reduce the number of synthetic steps ipso-chlorination reactions were tried. Reactions were carried out in dry tetrachloromethane with sulfuryl chloride in the presence of Lewis acids (AlCl3, FeCl3, PCl5). Results: It was shown that PCl5 presence led to the best yield (57 A). It was almost two times higher than in the case of aluminum chloride use. Unfortunately, the reaction with FeCl3 did not give the individual product. Conclusion: A new method for synthesis of dichlorinated at the upper rim calix{[}4]arenes via ipso chlorination with sulfuryl chloride in the presence of phosphorous pentachloride was developed. The influence of other Lewis acids was studied. The number and position of chlorine atoms in the structure of obtained compounds were confirmed.

Author keywords:

ipso-Substitution; chlorination; sulfuryl chloride; halogenated calix{[}4]arene; chlorocalix{[}4]arene STEPWISE SYNTHESIS; PHENOLIC UNITS; DERIVATIVES

DOI:

10.2174/1570178613666161013144

Web of Science ID:

ISI:000391709300002

Соавторы в МНС:

Другие поля

Поле	Значение
Publisher	BENTHAM SCIENCE PUBL LTD
Address	EXECUTIVE STE Y-2, PO BOX 7917, SAIF ZONE, 1200 BR SHARJAH, U ARAB EMIRATES
Language	English
EISSN	1875-6255
Keywords-Plus	STEPWISE SYNTHESIS; PHENOLIC UNITS; DERIVATIVES
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	e.a.ivanova@urfu.ru
Funding-Acknowledgement	Act 211 Government of the Russian Federation {[}02.A03.21.0006]; State task of Ministry of Education and Science {[}4.560.2014/K, 2014/236 (67)]
Funding-Text	The work was supported by Act 211 Government of the Russian Federation, contract No 02.A03.21.0006, State task of Ministry of Education and Science No 4.560.2014/K as well as No 2014/236 (67).
Number-of-Cited-References	13
Usage-Count-Last-180-days	6
Usage-Count-Since-2013	6
Journal-ISO	Lett. Org. Chem.
Doc-Delivery-Number	EH3YY