Reactions of perfluorobenzocycloalkenes with ethyl cyanoacetate and methyllithium and some transformations of the products

Reactions of perfluorobenzocycloalkenes with ethyl cyanoacetate and methyllithium and some transformations of the products Full article

Journal

Russian Journal of Organic Chemistry
ISSN: 1070-4280 , E-ISSN: 1608-3393

Output data

Year: 2013, Volume: 49, Number: 7, Pages: 1010-1018 Pages count : 9 DOI: 10.1134/S1070428013070099

Authors

Sinyakov V.R. ¹ , Zonov Ya.V. ^1,2 , Karpov V.M. ¹ , Beregovaya I.V. ¹ , Platonov V.E. ¹

Affiliations

1	(Данные Web of science) Russian Acad Sci, Siberian Branch, Vorozhtsov Novosibirsk Inst Organ Chem, Novosibirsk 630090, Russia
2	(Данные Web of science) Novosibirsk State Univ, Novosibirsk 630090, Russia

Reactions of perfluorobenzocycloalkenes (ArFF) with methyllithium and ethyl cyanoacetate involved replacement of fluorine atoms in positions 3 and 4 of perfluorocyclobutabenzene, position 5 of perfluoroindan, and position 6 of perfluorotetralin by CH3 and CH(CN)COOEt groups. Hydrolysis of the resulting esters ArFCH(CN)COOEt gave the corresponding perfluoroarylacetic acids ArFCH2COOH which were converted into dichloroacetyl chlorides ArFCCl2COCl by treatment with PCl5. The reaction of ArFCCl2COCl with SbF5 produced trifluoromethyl derivatives ArFCF3. Decarboxylation of ArFCCl2COOH in DMF afforded dichloromethyl derivatives ArFCCl2H which reacted with CsF on heating to form difluoromethyl analogs ArFCF2H.

Sinyakov V.R. , Zonov Y.V. , Karpov V.M. , Beregovaya I.V. , Platonov V.E.
Reactions of perfluorobenzocycloalkenes with ethyl cyanoacetate and methyllithium and some transformations of the products
Russian Journal of Organic Chemistry. 2013. V.49. N7. P.1010-1018. DOI: 10.1134/S1070428013070099 WOS Scopus РИНЦ

Синяков В.Р. , Зонов Я.В. , Карпов В.М. , Береговая И.В. , Платонов В.Е.
Взаимодействие перфторбензоциклоалкенов с цианоуксусным эфиром и метиллитием и некоторые превращения образующихся соединений
Журнал органической химии (RUSS J ORG CHEM+). 2013. Т.49. №7. С.1026-1034. РИНЦ

Published print:	Jul 1, 2013
Published online:	Aug 8, 2013

Web of science	WOS:000323061600009
Scopus	2-s2.0-84882276982
Elibrary	20458063
OpenAlex	W2065531295