Reaction of bistrifluoromethylaminosulphenyl chloride with fluoro-olefins and hexafluorobut-2-yne under free-radical conditions

✍ Scribed by Colin F. Service; Anthony E. Tipping

• Publisher: Elsevier Science
• Year: 1982
• Tongue: English
• Weight: 209 KB
• Volume: 20
• Category: Article
• ISSN: 0022-1139
• DOI: 10.1016/s0022-1139(00)84027-0

✦ Synopsis

Reaction of bistrifluoromethylaminosulphenyl chloride with unsymmetrical fluoro-olefins in daylight or under photochemical conditions gives both possible I:1 adducts (ca. I:1 ratio) arising from homolytic fission of the S-Cl bond. Addition to octafluorobut-2-ene and hexafluorobut-2-yne gives mixtures of the so& and anti-adducts. The reaction of bistrifluoromethylaminosulphenyl chloride (CF3)2NSC1 (I) with ethylene at 70 'C did not result in I:1 adduct formation but gave the compounds [(cF$~N]~s (II), (CF3)2NH, CF3N=CF2, SiF4 and (ClCH2CH2)2S [I]. However, treatment of a series of hydrocarbon olefins with the sulphenyl chloride (I) at -78 'C in the dark (ionic conditions) resulted in the formation of I:1 adducts in high yield and it was