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US 2003/0114721 A1Published application
Method for functionalising a double bond
OwnerNicolas Roquesinventor
Life of this patent
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Abstract
The invention concerns a method for functionalizing a double bond and, more particularly, a double bond bearing a metalloid atom. Said functionalization is produced by the action of perhalogenated sulphonyl chloride on the carbon bearing sulphur in the presence of a free radical initiator, preferably by homolytic cleavage. The invention is useful in organic synthesis.
Claims11
A process for functionalizing a double bond corresponding to formula I:
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- in which R1, R2 and R3, which may be identical or different, are chosen from hydrogen and hydrocarbyls attached to said double bond via an sp3 carbon;
- in which z is chosen from:
- halogens, advantageously chlorine and fluorine;
- residues such that ZH is an oxygenated acid;
- radicals of formula (CHR′)m-Ξ with Ξ chosen from halogens;
- and radicals of formula (CHR′)m—Y(O)q—R4 in which
- Y is a chalcogen, advantageously a light chalcogen;
- q is zero or an integer not more than 3, advantageously not more than 2 and preferably not more than 1, with the condition that when Y is oxygen, q is equal to zero;
- R′ represents a hydrocarbyl, advantageously of not more than four carbons, or preferably a hydrogen;
- m is equal to 1 or preferably to zero;
- and R4 is chosen from a hydrocarbyl or silyl group;
- by the action of sulfonyl chloride perhalogenated on the sulfur-bearing carbon (of the sulfonyl function) in the presence of a free-radical initiator, preferably by homolytic cleavage.
10 more elements
A compound of formula (II):
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- with R1, R2, Z and Rf being chosen from the same values (and with the same preferences) as above, but with the following additional conditions:
- with R1 and R2 chosen from hydrogen and hydrocarbyl radicals, with the condition that one of the radicals R1 or R2 at least is equal to H, and advantageously both of them;
- with Z chosen from radicals of formula (CHR′)m—Y—R4 in which R4Y is such that R4YH is an oxygenated acid, the possible aromatic nucleus (nuclei) being separated from said double bond by at least two atoms of sp3 hybridization (in the case of Z, an oxygen atom and at least one carbon atom, advantageously at least two sp3 carbon atoms;
- in the other cases, at least two sp3 carbon atoms);
- the total carbon number of the molecule being at least equal to (6−m) and not more than 30. Use of a compound of formula (II) in which m is equal to 1, to prepare a 3-perfluoroalkyl-1,2-epoxypropane:
3 more elements
A compound of formula (III)
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The use of compounds of formula (III) to prepare a 3-perfluoroalkyl-1,2-epoxypropane.
Dependencies are inferred from the claim text.