Compounds comprising a thiocarbonyl-sulfanyl group which can be used for the radical synthesis of α-perfluoroalkylamine compounds

A method for introducing a radical having the formula

• wherein X, Z4 and Rf are as defined below, into an olefin
• the method comprising reacting said olefin with a compound having the formula (I):
• to produce a compound of formula (II)
• where:
• X represents a member selected from the group consisting of a group —NZ2Z3, a group OZ5, and a halogen atom, where the halogen atom is selected from the group consisting of chlorine, bromine and iodine, where
• Z2 and Z3 are, independently of each other, a member selected from the group consisting of a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group oxygen, sulfur, selenium, tellurium, nitrogen, phosphorus, and arsenic;
• and
• Z5 represents a hydrogen atom, an alkyl group, a cycloalkyl group, aryl group, or a group which is electroattractive with respect to the oxygen atom to which it is bonded,
• Z1 represents a group selected from:
• (i) an alkyl, acyl, aryl, aralkyl, alkene, alkyne, cyclic hydrocarbon or heterocycle,
• (ii) a —ORa or —SRa group in which Ra is a group selected from the group consisting of:
• (a) alkyl, halogenoalkyl, alkenyl, alkynyl, acyl, aryl, arylalkyl, arylalkenyl, arylalkynyl, a cyclic hydrocarbon, a heterocycle and a polymer chain;
• (b) a —CRbRcPO(ORd)(ORe) group in which:
• Rb and Rc each represent, independently of each other, a hydrogen atom, a halogen atom, an alkyl, perfluoroalkyl, a cyclic hydrocarbon, a heterocycle, —NO2, —NCO, CN, —Rf, —SO3Rf, —SRf, —NRfRg, —COORf, —O2CRf, —CONRfRg, or —NCORfRg group, in which Rf and Rg each independently represent an alkyl, alkenyl, alkynyl, cycloalkenyl, cycloalkynyl, or an aryl group which is optionally condensed to a heterocycle, alkaryl, arylalkyl, heteroaryl,
• or Rb and Rc form, together with the carbon atom to which they are attached, a C═O group, a C═S group, a cyclic hydrocarbon or a heterocycle;
• and
• Rd and Re each represent, independently of each other, a radical which has the same the definition as the group Rf;
• or Rd and Re together form a hydrocarbon chain which comprises from 2 to 4 carbon atoms, and which is optionally interrupted by a group selected from —O—, —S— and —NRh—;
• in which Rh has the same definition as the group Rf;
• and
• (iii) a group —NRiRJ, in which:
• Ri and RJ represent, independently of each other, an alkyl, halogenoalkyl, alkenyl, alkynyl, acyl, ester, aryl, arylalkyl, arylalkenyl, arylalkynyl, cyclic hydrocarbon or a heterocycle group;
• or
• Ri and RJ together form a hydrocarbon chain which comprises from 2 to 4 carbon atoms and which is optionally interrupted by an O, S, or —NRH, or RH group, where the RH group has the same definition as the Rf group,
• Z4 represents a hydrogen atom, an alkyl or cycloalkyl group, and
• Rf represents
• (i) a halogen atom;
• (ii) fluoroalkyl;
• (iii) per-halogenated aryl radical, or
• (iv) a radical selected from RA—CF2—, RA—CF2—CF2—, RA—CF2—CF(CF3)—, CF3—C(RA)F— and (CF3)RA—, where RA is an alkyl, acyl, aryl, aralkyl, alkene, alkyne, cyclic hydrocarbon or a heterocycle,
• or a salt of compounds of formula (I).