Some highly fluorinated acyclic, cyclic, and polycyclic derivatives of Cl2NCF2CF2NCl2 and Cl2CNCCl2CCl2NCCl2

✍ Scribed by Ghulam Sarwar; Robert L. Kirchmeier; Jean'ne M. Shreeve

• Book ID: 102846397
• Publisher: John Wiley and Sons
• Year: 1990
• Tongue: English
• Weight: 603 KB
• Volume: 1
• Category: Article
• ISSN: 1042-7163
• DOI: 10.1002/hc.520010208

✦ Synopsis

Abstract

When Cl~2~NCF~2~CF~2~NCl~2~ is heated with CF~2~CFX (X = Cl, F) ClXCFCF~2~N(Cl)CF~2~CF~2~N(Cl)CF~2~CXClF (X = Cl, 2; F, 3) is formed. Mercury extracts chlorine fluoride from 2 and 3 to form new polyfluorobisazomethines, ClXCFCF~2~NCFCFNCF~2~CXClF (X = Cl, 4; F, 5). Photolysis of the product obtained from CCl~2~NCCl~2~CCl~2~NCCl~2~ with ClF, CF~2~ClN(Cl)CF ClCFClN(Cl)CF~2~Cl (6) gives another bisazomethine, CF~2~ClNCFCFNCF~2~Cl (7) with concomitant loss of Cl~2~. 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 CFCl~3~ to form (11), and 14 loses Cl~2~ 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).