The influence of fluorine and parahalogen substituents on the chemistry of some functional groups

Abstract

The influence of fluorine, trifluoromethyl, trifluoromethylsulfanyl or trifluoromethylselenyl on the chemistry of selected functional groups such as carbene, nitrene, CX (XO, S, Se, Te), CCO and NSO will be presented. Starting with evidence for the existence of (CF 3S) 2C and CF 3SN, their stability and reactivity will be compared with those of F- and CF 3-substituted carbenes and nitrenes. Tellurocarbonyldifluoride, (CF 3) 2CSe, (CF 3Se) 2CSe, (CF 3S) 2CCO and CF 3SNSO are other key compounds treated in the same manner. Their preparation and chemical and physical properties will be discussed in comparison with either their fluorine, CF 3, CF 3S or CF 3Se analogues. An attempt will be made to offer general rules for planning potentially successful syntheses.