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US 2008/0306281 A1Published application
Novel compounds comprising a thiocarbonyl-sulfanyl group which can be used for the radical synthesis of alpha-perfluoroalkylamine compounds
AssigneeRhodia Operations
InventorsSamir Zard, Fabien Gagosz, Lucie Tournier
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Abstract
The invention relates to compounds having the general formula (I), the method of preparation thereof and the use thereof in organic radical synthesis. The invention also relates to compounds having the formula (II), the method of preparation thereof and a method for preparing compounds having the formula (VIII).
Claims26
A method for introducing into an organic compound a radical having the formula
- wherein X, Z4 and Rf are as defined below,
- the method comprising reacting said organic compound with a compound having the formula (I):
- where:
- X represents a group which donates electrons by mesomeric effect;
- 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, —OR“, —SR”, —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, or 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 the definition as the group Rf;
- and
- (iii) a group —NRiRj, in which:
- Rl and Ri represent, independently of each other, an alkyl, halogenoalkyl, alkenyl, alkynyl, acyl, ester, aryl, arylalkyl, arylalkenyl, arylalkynyl, cyclic hydrocarbon or a heterocycle group;
- or
- Rl and Ri 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) a poly- or 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).
24 more elements
Dependencies are inferred from the claim text.