Using a combination of Kumada, Suzuki and Biellmann chemistry, various menaquinones can synthesised 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.

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.1═CR.sup.2—X—Rf.sup.2).sub.n—Y—Z (1), Rf.sup.1—(X—CR.sup.1═CR.sup.2—Rf.sup.2).sub.n—Y—Z (2) or Rf.sup.3—(CF═CR.sup.3—CR.sup.4═CF—Rf.sup.4).sub.n—Y—Z (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.1═CR.sup.2—X—Rf.sup.2).sub.n—Y—Z (1), Rf.sup.1—(X—CR.sup.1═CR.sup.2—Rf.sup.2).sub.n—Y—Z (2) or Rf.sup.3—(CF═CR.sup.3—CR.sup.4═CF—Rf.sup.4).sub.n—Y—Z (5); and a surface modifier using the compound.

Provided is a composition that contains a fluoroethylene having one or more fluorine atoms, the composition having excellent stability of the fluoroethylene. The fluoroethylene composition of the present disclosure contains a fluoroethylene having one or more fluorine atoms, water, and oxygen, the composition having a water content of 100 mass ppm or less based on the mass of the fluoroethylene, and an oxygen content of 0.35 mol % or less based on the fluoroethylene. The fluoroethylene composition has excellent stability of fluoroethylene.

Provided is a composition that contains a fluoroethylene having one or more fluorine atoms, the composition having excellent stability of the fluoroethylene. The fluoroethylene composition of the present disclosure contains a fluoroethylene having one or more fluorine atoms, water, and oxygen, the composition having a water content of 100 mass ppm or less based on the mass of the fluoroethylene, and an oxygen content of 0.35 mol % or less based on the fluoroethylene. The fluoroethylene composition has excellent stability of fluoroethylene.

The present invention provides a process for preparing 6-isopropenyl-3-methyl-9-decenyl acetate (5): wherein Ac represents an acetyl group, the process comprising steps of: subjecting a 2-methyl-2,6-heptadiene compound (1) having a leaving group X at position 1: wherein X represents an acyloxy group having 1 to 10 carbon atoms including the carbon atom of the carbonyl group, an alkanesulfonyloxy group having 1 to 10 carbon atoms, an arenesulfonyloxy group having 6 to 20 carbon atoms, or a halogen atom, to a nucleophilic substitution reaction with a 3-methylpentyl nucleophilic reagent (2) having a protected hydroxyl group at position 5: wherein M represents Li, MgZ.sup.1, ZnZ.sup.1, Cu, CuZ.sup.1, or CuLiZ.sup.1, wherein Z.sup.1 represents a halogen atom or a CH.sub.2CH.sub.2CH(CH.sub.3)CH.sub.2CH.sub.2OR group, and R represents a protecting group for a hydroxyl group, to form a 6-isopropenyl-3-methyl-9-decene compound (3) having a protected hydroxyl group at position 1: wherein R is as defined above; subjecting the 6-isopropenyl-3-methyl-9-decene compound (3) having the protected hydroxyl group at position 1 to a deprotection reaction to form 6-isopropenyl-3-methyl-9-decenol (4); and acetylating 6-isopropenyl-3-methyl-9-decenol (4) to form 6-isopropenyl-3-methyl-9-decenyl acetate (5).

##STR00001##

The present invention provides a process for preparing 6-isopropenyl-3-methyl-9-decenyl acetate (5): wherein Ac represents an acetyl group, the process comprising steps of: subjecting a 2-methyl-2,6-heptadiene compound (1) having a leaving group X at position 1: wherein X represents an acyloxy group having 1 to 10 carbon atoms including the carbon atom of the carbonyl group, an alkanesulfonyloxy group having 1 to 10 carbon atoms, an arenesulfonyloxy group having 6 to 20 carbon atoms, or a halogen atom, to a nucleophilic substitution reaction with a 3-methylpentyl nucleophilic reagent (2) having a protected hydroxyl group at position 5: wherein M represents Li, MgZ.sup.1, ZnZ.sup.1, Cu, CuZ.sup.1, or CuLiZ.sup.1, wherein Z.sup.1 represents a halogen atom or a CH.sub.2CH.sub.2CH(CH.sub.3)CH.sub.2CH.sub.2OR group, and R represents a protecting group for a hydroxyl group, to form a 6-isopropenyl-3-methyl-9-decene compound (3) having a protected hydroxyl group at position 1: wherein R is as defined above; subjecting the 6-isopropenyl-3-methyl-9-decene compound (3) having the protected hydroxyl group at position 1 to a deprotection reaction to form 6-isopropenyl-3-methyl-9-decenol (4); and acetylating 6-isopropenyl-3-methyl-9-decenol (4) to form 6-isopropenyl-3-methyl-9-decenyl acetate (5).

##STR00001##

According to a method for producing a perfluoroalkadiene compound represented by general formula (1): CF.sub.2═CF—(CF.sub.2).sub.n-4—CF═CF.sub.2 (1), wherein n is an integer of 4 or more, the method comprising a reaction step of adding a nitrogen-containing compound to a solution of a compound represented by general formula (2): X.sup.1CF.sub.2—CFX.sup.2—(CF.sub.2).sub.n-4—CF.sub.2—CF.sub.2X.sup.1 (2), wherein n is the same as above, X.sup.1 is the same or different and is a halogen atom other than fluorine, and X.sup.2 is a halogen atom, the perfluoroalkadiene compound can be obtained at a high yield.

According to a method for producing a perfluoroalkadiene compound represented by general formula (1): CF.sub.2═CF—(CF.sub.2).sub.n-4—CF═CF.sub.2 (1), wherein n is an integer of 4 or more, the method comprising a reaction step of adding a nitrogen-containing compound to a solution of a compound represented by general formula (2): X.sup.1CF.sub.2—CFX.sup.2—(CF.sub.2).sub.n-4—CF.sub.2—CF.sub.2X.sup.1 (2), wherein n is the same as above, X.sup.1 is the same or different and is a halogen atom other than fluorine, and X.sup.2 is a halogen atom, the perfluoroalkadiene compound can be obtained at a high yield.

According to a method for producing a perfluoroalkadiene compound represented by general formula (1): CF.sub.2═CF—(CF.sub.2).sub.n-4—CF═CF.sub.2 (1), wherein n is an integer of 4 or more, the method comprising a reaction step of adding a nitrogen-containing compound to a solution of a compound represented by general formula (2): X.sup.1CF.sub.2—CFX.sup.2—(CF.sub.2).sub.n-4—CF.sub.2—CF.sub.2X.sup.1 (2), wherein n is the same as above, X.sup.1 is the same or different and is a halogen atom other than fluorine, and X.sup.2 is a halogen atom, the perfluoroalkadiene compound can be obtained at a high yield.