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- Title
Reactions of perfluorobenzocycloalkenes with ethyl cyanoacetate and methyllithium and some transformations of the products.
- Authors
Sinyakov, V.; Zonov, Ya.; Karpov, V.; Beregovaya, I.; Platonov, V.
- Abstract
Reactions of perfluorobenzocycloalkenes (ArF) 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 CH and CH(CN)COOEt groups. Hydrolysis of the resulting esters ArCH(CN)COOEt gave the corresponding perfluoroarylacetic acids ArCHCOOH which were converted into dichloroacetyl chlorides ArCClCOCl by treatment with PCl. The reaction of ArCClCOCl with SbF produced trifluoromethyl derivatives ArCF. Decarboxylation of ArCClCOOH in DMF afforded dichloromethyl derivatives ArCClH which reacted with CsF on heating to form difluoromethyl analogs ArCFH.
- Subjects
METHYL acetate; METHYLLITHIUM; CYCLOALKANES; FLUORINE; HYDROLYSIS; ACETIC acid
- Publication
Russian Journal of Organic Chemistry, 2013, Vol 49, Issue 7, p1010
- ISSN
1070-4280
- Publication type
Academic Journal
- DOI
10.1134/S1070428013070099