The present disclosure provides compounds, compositions, and methods for preparing alkenyl halides and/or haloalkyl-substituted olefins with Z-selectivity. The methods are particularly useful for preparing alkenyl fluorides such as CF.sub.3-substituted olefins by means of cross-metathesis reactions using halogen-containing molybdenum and tungsten complexes.

The present disclosure provides compounds, compositions, and methods for preparing alkenyl halides and/or haloalkyl-substituted olefins with Z-selectivity. The methods are particularly useful for preparing alkenyl fluorides such as CF.sub.3-substituted olefins by means of cross-metathesis reactions using halogen-containing molybdenum and tungsten complexes.

The present disclosure provides methods for preparing polyunsaturated hydrocarbons, such as E,E-farnesol, farnesyl acetate and squalene, by base catalyzed addition of a dialkylamine to a 3-methylene-1-alkene, such as farnesene. The present disclosure also provides compositions including one more farnesene derivatives prepared using the disclosed methods.

The present disclosure provides methods for preparing polyunsaturated hydrocarbons, such as E,E-farnesol, farnesyl acetate and squalene, by base catalyzed addition of a dialkylamine to a 3-methylene-1-alkene, such as farnesene. The present disclosure also provides compositions including one more farnesene derivatives prepared using the disclosed methods.

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.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.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.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.

Provided is a method for producing hexafluoro-1,3-butadiene, and the method can produce hexafluoro-1,3-butadiene at an industrially sufficient level of yield. In a reaction liquid containing a halogenated butane represented by chemical formula, CF.sub.2X.sup.1CFX.sup.2CFX.sup.3CF.sub.2X.sup.4 (X.sup.1, X.sup.2, X.sup.3, and X.sup.4 are each independently a halogen atom other than a fluorine atom), zinc, and an organic solvent, a reaction is conducted to eliminate the halogen atoms other than a fluorine atom, X.sup.1, X.sup.2, X.sup.3, and X.sup.4, from the halogenated butane, yielding hexafluoro-1,3-butadiene. During the reaction, the concentration of a zinc halide generated by the reaction, in the reaction liquid is not more than the solubility of the zinc halide in the organic solvent.

Provided is a method for producing hexafluoro-1,3-butadiene, and the method can produce hexafluoro-1,3-butadiene at an industrially sufficient level of yield. In a reaction liquid containing a halogenated butane represented by chemical formula, CF.sub.2X.sup.1CFX.sup.2CFX.sup.3CF.sub.2X.sup.4 (X.sup.1, X.sup.2, X.sup.3, and X.sup.4 are each independently a halogen atom other than a fluorine atom), zinc, and an organic solvent, a reaction is conducted to eliminate the halogen atoms other than a fluorine atom, X.sup.1, X.sup.2, X.sup.3, and X.sup.4, from the halogenated butane, yielding hexafluoro-1,3-butadiene. During the reaction, the concentration of a zinc halide generated by the reaction, in the reaction liquid is not more than the solubility of the zinc halide in the organic solvent.

A process to prepare (9E,11Z)-9,11-hexadecadienyl acetate with a good yield and high purity of the general formula (1): CH.sub.3(CH.sub.2).sub.3CHCHCHCH(CH.sub.2).sub.aX.=The process includes a step of conducting a Wittig reaction between a haloalkenal of the general formula (2): OHCCHCH(CH.sub.2).sub.aX, and a triarylphosphonium pentylide of the general formula (3): CH.sub.3(CH.sub.2).sub.3CH.sup.P.sup.+Ar.sub.3, to obtain the 1-haloalkadiene, and the use of a (7E,9Z)-1-halo-7,9-tetradecadiene obtained by the process for a process of preparing (9E, 11Z)-9,11-hexadecadienyl acetate.