W. Dmowski, I. Nowak, P. Jones
Feb 1, 1996
Citations
0
Influential Citations
2
Citations
Journal
Journal of Fluorine Chemistry
Abstract
Abstract Treatment of trans-4,5-dibromo-cis-1,2-cyclohexanedicarboxylic anhydride (2) with SF4 and HF resulted in fluorination of the carbonyl groups and the almost total replacement of one bromine atom by fluorine affording 3-bromo-4,7,7,9,9-pentafluoro-8-oxa-cis-bicyclo[4.3.0]nonane (3) and 1-bromo-2-fluoro-cis-4,5-bis (trifluoromethyl)cyclohexane (4) in a 5:1 ratio with only trace amounts of 1,2-dibromo-cis-4,5-bis-(trifluoromethyl)cyclohexane (5). Dehalogenation of this mixture with zinc gave a mixture of 7,7,9,9-tetrafluoro-8-oxa-cis-bicyclo[4.3.0]non-3-ene (6) and cis-4,5-bis(trifluoro-methyl)cyclohex-1-ene (7). Pure 6 was isolated by bromination and subsequent separation of the dibromo derivatives by crystallization and debromination. The structure of isomer 3a was confirmed by X-ray analysis.