Pentafluorophenylation of perfluorinated benzocyclobutene, indan, and tetralin by reaction with pentafluorobenzene in SbF5

Pentafluorophenylation of perfluorinated benzocyclobutene, indan, and tetralin by reaction with pentafluorobenzene in SbF5 Full article

Journal

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

Output data

Year: 2002, Volume: 38, Number: 8, Pages: 1158-1165 Pages count : 8 DOI: 10.1023/A:1020901526459

Authors

Karpov V.M. ¹ , Mezhenkova T.V. ¹ , Platonov V.E. ¹ , Sinyakov V.R. ¹ , Shchegoleva L.N. ¹

Affiliations

1	(Данные Web of science) Russian Acad Sci, Siberian Dept, Vorozhtsov Novosibirsk Inst Organ Chem, Novosibirsk 630090, Russia

The reactivity of perfluorinated benzocyclobutene, indan, and tetralin in reaction with pentafluorobenzene in SbF5 medium, and also the relative stability of generated therewith perfluoro-1-phenyl-benzocycloalkenyl cations decrease with increasing alicyclic fragment in the benzocycloalkene. Treating the solutions of salts of the above cations with anhydrous HF results in the corresponding perfluoro-1-phenylbenzocycloalkenes, and the hydrolysis of salts furnishes their 1-hydroxy derivatives. In a reaction of 1-hydroxyperfluoro-1-phenylbenzocyclobutene, -indan, and -tetralin with SOCl2 the hydroxy group is replaced by chlorine. Besides with indan and tetralin derivatives form respectively 7-pentafluorophenyl-octafluoro-3-chlorobicyclo[4.3.0]hepta- 1,4,6-triene and 7-pentafluorophenyldecafluoro-3-chlorobicyclo[4.4.0]octa-1,4,6-triene.

Karpov V.M. , Mezhenkova T.V. , Platonov V.E. , Sinyakov V.R. , Shchegoleva L.N.
Pentafluorophenylation of perfluorinated benzocyclobutene, indan, and tetralin by reaction with pentafluorobenzene in SbF5
Russian Journal of Organic Chemistry. 2002. V.38. N8. P.1158-1165. DOI: 10.1023/A:1020901526459 WOS Scopus РИНЦ

Web of science	WOS:000179993700015
Scopus	2-s2.0-0036412387
Elibrary	13415453
OpenAlex	W2950418988