RfS-substituted furanes, pyrroles and imidazoles; the tetrakis(trifluoromethylmercapto)pyrrole-radical

✍ Scribed by D.M. Ceacareanu; M.R.C. Gerstenberger; A. Haas

• Publisher: Elsevier Science
• Year: 1980
• Tongue: English
• Weight: 40 KB
• Volume: 16
• Category: Article
• ISSN: 0022-1139
• DOI: 10.1016/s0022-1139(00)84055-5

✦ Synopsis

Reactions of perchlorofluoromethanesulfenylchlorides

CClnF3 ,SCl (n = O-2) with the heterocycles furane, pyrrole and imidazole under varying conditions yield a broad pattern of substitution products. The formation thereof as well as some by-products are briefly discussed. In case of pyrrole-nucleus and CF3SC1 up to four-fold substitution is performed yielding 2,3,4,5-tetrakis(trifluoromethylsulfenyl)pyrrole ( 'TTP' ). This interesting compound shows reaction behaviour determined by a moderately acidic proton bound to the ring nitrogen. 'TTP' by this way is able to form metal-salts (e.g. with Hg, Ag), adducts with bases (e.g. NH3, (CH3)3N, pyridine) and N-functional derivatives (e.g. with the (CH3)3Si-group). Furthermore the preparation of a !TTP"-radical is accomplished by oxidation of 'TTP' with reagents such as Pb02 or NiOx. ESR-and ENDORspectra are presented.