Use of a compound of Formula (I) in a nonaqueous battery electrolyte formulation (1) wherein R is a fluorinated alkyl group and X is selected from the group consisting of F, Cl, H, CF.sub.3, and C.sub.1 to C.sub.6 alkyl which may be at least partially fluorinated and —OR group can be cis- or trans- to any other group X.

##STR00001##

The present invention relates to a fluorine-containing diene compound represented by the following formula I, and to a polymer thereof. In the formula, each of R.sup.1 to R.sup.7 is independently a hydrogen atom, a chlorine atom, a fluorine atom, or an alkyl group having a carbon number of 1 to 5 which may be substituted by a fluorine atom, k is 0 or 1, and at least one of R.sup.1 to R.sup.7 is a hydrogen atom. ##STR00001##

The present invention relates to a fluorine-containing diene compound represented by the following formula I, and to a polymer thereof. In the formula, each of R.sup.1 to R.sup.7 is independently a hydrogen atom, a chlorine atom, a fluorine atom, or an alkyl group having a carbon number of 1 to 5 which may be substituted by a fluorine atom, k is 0 or 1, and at least one of R.sup.1 to R.sup.7 is a hydrogen atom. ##STR00001##

An alkoxyvinyl ether is disclosed having the chemical structure R.sub.fC(OR)═CHR.sub.f′, wherein R.sub.f is an at least partially fluorinated functional group having at least one carbon atom, R.sub.f′ is an at least partially fluorinated functional group having at least two carbon atoms, and R is a functional group. A method for preparing an alkoxyvinyl ether is disclosed, comprising R.sub.fCFHCFHR.sub.f′+KOH/ROH.fwdarw.R.sub.fC(OR)═CHR.sub.f′, wherein R.sub.f is a perfluoro functional group, R.sub.f′ is a perfluoro functional group, and R is an alkyl functional group. Another method for preparing an alkoxyvinyl ether is disclosed, comprising R.sub.fCF═CHR.sub.f′+KOH/ROH.fwdarw.R.sub.fC(OR)═CHR.sub.f′, wherein R.sub.f is a perfluoro functional group, R.sub.f′ is a perfluoro functional group, and R is an alkyl functional group.

An alkoxyvinyl ether is disclosed having the chemical structure R.sub.fC(OR)═CHR.sub.f′, wherein R.sub.f is an at least partially fluorinated functional group having at least one carbon atom, R.sub.f′ is an at least partially fluorinated functional group having at least two carbon atoms, and R is a functional group. A method for preparing an alkoxyvinyl ether is disclosed, comprising R.sub.fCFHCFHR.sub.f′+KOH/ROH.fwdarw.R.sub.fC(OR)═CHR.sub.f′, wherein R.sub.f is a perfluoro functional group, R.sub.f′ is a perfluoro functional group, and R is an alkyl functional group. Another method for preparing an alkoxyvinyl ether is disclosed, comprising R.sub.fCF═CHR.sub.f′+KOH/ROH.fwdarw.R.sub.fC(OR)═CHR.sub.f′, wherein R.sub.f is a perfluoro functional group, R.sub.f′ is a perfluoro functional group, and R is an alkyl functional group.

An object of the present invention is to provide, for example, a novel method for synthesizing a fluorovinyl ether compound from a fluorine-containing vinyl compound. This problem is solved by a method for producing a compound represented by formula (1):

##STR00001##

wherein
R.sup.a1 is a hydrogen atom, a halogeno group, an alkyl group, a fluoroalkyl group, or an aromatic group optionally having one or more substituents,
Rf is a fluoro group or a perfluoroalkyl group,
R.sup.a2 is a hydrogen atom, a halogeno group, an alkyl group, a fluoroalkyl group, or an aromatic group optionally having one or more substituents, or
(i) R.sup.a1 and R.sup.a2, (ii) R.sup.a1 and Rf, or (iii) Rf and R.sup.a2 may be linked to each other,
R.sup.b1 is R.sup.s,
R.sup.b2 is a hydrogen atom or R.sup.s,
R.sup.b3 is a hydrogen atom or R.sup.s, or
two or three of R.sup.b1, R.sup.b2, and R.sup.b3, taken together with the adjacent carbon atom, may form a ring optionally having one or more substituents, and
R.sup.s, in each occurrence, is the same or different and represents a hydrocarbon group optionally having one or more substituents, the method comprising
step A of reacting a compound represented by formula (2):

##STR00002##

wherein
R.sup.x is a leaving group, and
other symbols are as defined above,
with a compound represented by formula (3):

##STR00003##

wherein the symbols in the formula are as defined above,
in the presence of a transition metal catalyst.

An object of the present invention is to provide, for example, a novel method for synthesizing a fluorovinyl ether compound from a fluorine-containing vinyl compound. This problem is solved by a method for producing a compound represented by formula (1):

##STR00001##

wherein
R.sup.a1 is a hydrogen atom, a halogeno group, an alkyl group, a fluoroalkyl group, or an aromatic group optionally having one or more substituents,
Rf is a fluoro group or a perfluoroalkyl group,
R.sup.a2 is a hydrogen atom, a halogeno group, an alkyl group, a fluoroalkyl group, or an aromatic group optionally having one or more substituents, or
(i) R.sup.a1 and R.sup.a2, (ii) R.sup.a1 and Rf, or (iii) Rf and R.sup.a2 may be linked to each other,
R.sup.b1 is R.sup.s,
R.sup.b2 is a hydrogen atom or R.sup.s,
R.sup.b3 is a hydrogen atom or R.sup.s, or
two or three of R.sup.b1, R.sup.b2, and R.sup.b3, taken together with the adjacent carbon atom, may form a ring optionally having one or more substituents, and
R.sup.s, in each occurrence, is the same or different and represents a hydrocarbon group optionally having one or more substituents, the method comprising
step A of reacting a compound represented by formula (2):

##STR00002##

wherein
R.sup.x is a leaving group, and
other symbols are as defined above,
with a compound represented by formula (3):

##STR00003##

wherein the symbols in the formula are as defined above,
in the presence of a transition metal catalyst.

The present application provides, among other things, compounds and methods for metathesis reactions. In some embodiments, the present disclosure provides methods for preparing alkenyl halide with regioselectivity and/or stereoselectivity. In some embodiments, the present disclosure provides methods for preparing alkenyl halide with regioselectivity and Z-selectivity. In some embodiments, the present disclosure provides methods for preparing alkenyl halide with regioselectivity and E-selectivity. In some embodiments, provided technologies are particularly useful for preparing alkenyl fluorides. In some embodiments, a provided compound useful for metathesis reactions has the structure of formula II-a. In some embodiments, a provided compound useful for metathesis reactions has the structure of formula II-b.

The present application provides, among other things, compounds and methods for metathesis reactions. In some embodiments, the present disclosure provides methods for preparing alkenyl halide with regioselectivity and/or stereoselectivity. In some embodiments, the present disclosure provides methods for preparing alkenyl halide with regioselectivity and Z-selectivity. In some embodiments, the present disclosure provides methods for preparing alkenyl halide with regioselectivity and E-selectivity. In some embodiments, provided technologies are particularly useful for preparing alkenyl fluorides. In some embodiments, a provided compound useful for metathesis reactions has the structure of formula II-a. In some embodiments, a provided compound useful for metathesis reactions has the structure of formula II-b.

The production of solvents for applications such as heat transfer, cleaning, and degreasing, for example. In particular, the production of solvents derived from 1-chloro-3,3,3-trifluoro-propene, such as chloro and/or fluoro substituted alkanes and chloro and/or fluoro substituted trifluoropropenyl ethers.