ISSN:
1572-8838
Source:
Springer Online Journal Archives 1860-2000
Topics:
Chemistry and Pharmacology
,
Electrical Engineering, Measurement and Control Technology
Notes:
Abstract Fluorine containing-cyclohexadienes (FCHDs), 3,3,6,6,-tetrafluoro-1,4-cyclohexadiene (1a), 1-chloro-3,3,6,6-tetrafluoro-1,4-cyclohexadiene (3a) and 1-bromo-3,3,6,6-tetrafluoro-1,4-cyclohexadiene (4a), were isolated in pure states with high yields (ca. 80%) by the preparative scale electrochemical fluorination of 1,4-difluorobenzene (1), 1-chloro-2,5-difluorobenzene (3) and 1-bromo-2,5-difluorobenzene (4), respectively, in Et4NF · mHF (Et = C2H5: m = 4.0, 4.45 and 4.7) at a platinum anode, followed by extraction and fractional distillation. The electrochemical fluorination of 1,2,4-trifluorobenzene (2) yielded both 1,3,3,6,6-pentafluoro-1,4-cyclohexadiene (2a) and 2,5,5,6,6-pentafluoro-1,3-cyclohexadiene (2b) with high yield (ca. 90%). Some of (2a) was also isolated in a pure state by fractional distillation. Each substrate compound (1–4) was fluorinated to the corresponding FCHDs with an almost quantitative yield when 2.0–2.1 faraday (per mol of substrate) of electricity was passed.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1007/BF00241926
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