Using a combination of Kumada, Suzuki and Biellmann chemistry, various menaquinones can synthesized rapidly and with stereochemical integrity offering a new way of preparing these vitamin K2 components for the pharmaceutical market. In one embodiment a process for the preparation of a compound of formula (I) ##STR00001## is defined including a step in which (i) a compound of formula (II) is reacted with a compound of formula (III) ##STR00002## wherein R is an alkyl group; LG is a leaving group; m is an integer from 0 to 8; n is an integer of from 0 to 9; and X is hydrogen, halide, hydroxyl or protected hydroxyl; in the presence of a copper, nickel or palladium catalyst.

Using a combination of Kumada, Suzuki and Biellmann chemistry, various menaquinones can synthesized rapidly and with stereochemical integrity offering a new way of preparing these vitamin K2 components for the pharmaceutical market. In one embodiment a process for the preparation of a compound of formula (I) ##STR00001## is defined including a step in which (i) a compound of formula (II) is reacted with a compound of formula (III) ##STR00002## wherein R is an alkyl group; LG is a leaving group; m is an integer from 0 to 8; n is an integer of from 0 to 9; and X is hydrogen, halide, hydroxyl or protected hydroxyl; in the presence of a copper, nickel or palladium catalyst.

A compound of formula (I): (I) wherein n is an integer between 0 and 10; Y is hydrogen, halide, mesylate, tosylate, ester, SPh, SO2Ph, hydroxyl or protected hydroxyl; with the proviso that if n=0 or 1, Y is not hydrogen.

##STR00001##

A compound of formula (I): (I) wherein n is an integer between 0 and 10; Y is hydrogen, halide, mesylate, tosylate, ester, SPh, SO2Ph, hydroxyl or protected hydroxyl; with the proviso that if n=0 or 1, Y is not hydrogen.

##STR00001##

To provide a novel fluorine-containing compound that does not include any long chain perfluoroalkyl unit having 8 or more carbon atoms, which is problematic in terms of the environment, and that is excellent in water repellency/oil repellency, and a surface modifier using the compound. [Solution] There are used a fluorine-containing compound represented by the following general formula (1), the following general formula (2) or the following general formula (5): Rf.sup.1(CR.sup.1CR.sup.2XRf.sup.2).sub.nYZ (1), Rf.sup.1(XCR.sup.1CR.sup.2Rf.sup.2).sub.nYZ (2) or Rf.sup.3(CFCR.sup.3CR.sup.4CFRf.sup.4).sub.nYZ (5); and a surface modifier using the compound.

To provide a novel fluorine-containing compound that does not include any long chain perfluoroalkyl unit having 8 or more carbon atoms, which is problematic in terms of the environment, and that is excellent in water repellency/oil repellency, and a surface modifier using the compound. [Solution] There are used a fluorine-containing compound represented by the following general formula (1), the following general formula (2) or the following general formula (5): Rf.sup.1(CR.sup.1CR.sup.2XRf.sup.2).sub.nYZ (1), Rf.sup.1(XCR.sup.1CR.sup.2Rf.sup.2).sub.nYZ (2) or Rf.sup.3(CFCR.sup.3CR.sup.4CFRf.sup.4).sub.nYZ (5); and a surface modifier using the compound.

The present invention relates to a method for the chemical conversion of an unsaturated fatty acid, particularly a carbon chain extension reaction. According to the present invention, a method for extending the length of a carbon chain in an unsaturated fatty acid by two carbon atoms is provided, said method comprising a step of heating a malonic acid ester derivative of an unsaturated fatty acid to reflux in a lower fatty acid solution in the presence of an antioxidative agent. It is preferred that the unsaturated fatty acid is an unsaturated fatty acid having 16 to 24 carbon atoms. It is preferred that the unsaturated fatty acid is selected from the group consisting of linoleic acid, linolenic acid, arachidonic acid, stearidonic acid, icosatetraenoic acid, icosapentaenoic acid, tetracosahexaenoic acid and docosahexaenoic acid. According to the method of the present invention, a carbon chain extension reaction can be completed within a shorter time.

The present invention relates to a method for the chemical conversion of an unsaturated fatty acid, particularly a carbon chain extension reaction. According to the present invention, a method for extending the length of a carbon chain in an unsaturated fatty acid by two carbon atoms is provided, said method comprising a step of heating a malonic acid ester derivative of an unsaturated fatty acid to reflux in a lower fatty acid solution in the presence of an antioxidative agent. It is preferred that the unsaturated fatty acid is an unsaturated fatty acid having 16 to 24 carbon atoms. It is preferred that the unsaturated fatty acid is selected from the group consisting of linoleic acid, linolenic acid, arachidonic acid, stearidonic acid, icosatetraenoic acid, icosapentaenoic acid, tetracosahexaenoic acid and docosahexaenoic acid. According to the method of the present invention, a carbon chain extension reaction can be completed within a shorter time.

A method of forming homoallylic compounds 2 from cyclopropylvinyl precursors 1 in the presence of a Bronsted acid HQ ##STR00001##

A method of forming homoallylic compounds 2 from cyclopropylvinyl precursors 1 in the presence of a Bronsted acid HQ ##STR00001##