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- Publisher
- Wiley
- Copyright
- Copyright © 1990 Wiley Subscription Services
- ISSN
- 1042-7163
- eISSN
- 1098-1071
- DOI
- 10.1002/hc.520010208
- Publisher site
- See Article on Publisher Site
Abstract
When Cl2NCF2CF2NCl2 is heated with CF2CFX (X = Cl, F) ClXCFCF2N(Cl)CF2CF2N(Cl)CF2CXClF (X = Cl, 2; F, 3) is formed. Mercury extracts chlorine fluoride from 2 and 3 to form new polyfluorobisazomethines, ClXCFCF2NCFCFNCF2CXClF (X = Cl, 4; F, 5). Photolysis of the product obtained from CCl2NCCl2CCl2NCCl2 with ClF, CF2ClN(Cl)CF ClCFClN(Cl)CF2Cl (6) gives another bisazomethine, CF2ClNCFCFNCF2Cl (7) with concomitant loss of Cl2. At 25°C, in the presence of CsF, 4 and 5 are cyclized to give (X = Cl, 8; F, 9), and 7 forms a bicyclic derivative at 100°C, (1). Addition of chlorine fluoride to 8 and to 1 produces (10) and (14), respectively. Photolysis of 10 results in the loss of CFCl3 to form (11), and 14 loses Cl2 and dimerizes to the hydrazine (15). The further addition of ClF to 11 gives rise to (12) which when photolyzed at 3000 Å forms a second cyclic hydrazine, (13).
Journal
Heteroatom Chemistry – Wiley
Published: Jan 1, 1990