An object of the present invention is to provide a novel method for producing a fluorine-containing methylene compound. The above object can be achieved by a method for producing a compound represented by formula (1): ##STR00001##
wherein R.sup.1 represents an organic group, R.sup.A represents hydrogen or fluorine, R.sup.4a represents hydrogen or an organic group, R.sup.4b represents hydrogen or an organic group, R.sup.5a represents hydrogen or an organic group, R.sup.5b represents hydrogen or an organic group, and
R.sup.2 represents hydrogen or an organic group; R.sup.2 is optionally connected to R.sup.4a to form a ring; the method comprising step A of reacting a compound represented by formula (2): ##STR00002##
wherein X.sup.1 represents a leaving group, and other symbols are as defined above, with a compound represented by formula (3): ##STR00003##
wherein X.sup.2 represents a leaving group, and other symbols are as defined above, in the presence of a reducing agent as desired, under light irradiation.

An object of the present invention is to provide a novel method for producing a fluorine-containing methylene compound. The above object can be achieved by a method for producing a compound represented by formula (1): ##STR00001##
wherein R.sup.1 represents an organic group, R.sup.A represents hydrogen or fluorine, R.sup.4a represents hydrogen or an organic group, R.sup.4b represents hydrogen or an organic group, R.sup.5a represents hydrogen or an organic group, R.sup.5b represents hydrogen or an organic group, and
R.sup.2 represents hydrogen or an organic group; R.sup.2 is optionally connected to R.sup.4a to form a ring; the method comprising step A of reacting a compound represented by formula (2): ##STR00002##
wherein X.sup.1 represents a leaving group, and other symbols are as defined above, with a compound represented by formula (3): ##STR00003##
wherein X.sup.2 represents a leaving group, and other symbols are as defined above, in the presence of a reducing agent as desired, under light irradiation.

Disclosed herein are methods for synthesizing fatty olefin metathesis products of high Z-isomeric purity from olefin feedstocks of low Z-isomeric purity. The methods include contacting a contacting an olefin metathesis reaction partner, such as acylated alkenol or an alkenal acetal, with an internal olefin in the presence of a Z-selective metathesis catalyst to form the fatty olefin metathesis product. In various embodiments, the fatty olefin metathesis products are insect pheromones. Pheromone compositions and methods of using them are also described.

Disclosed herein are methods for synthesizing fatty olefin metathesis products of high Z-isomeric purity from olefin feedstocks of low Z-isomeric purity. The methods include contacting a contacting an olefin metathesis reaction partner, such as acylated alkenol or an alkenal acetal, with an internal olefin in the presence of a Z-selective metathesis catalyst to form the fatty olefin metathesis product. In various embodiments, the fatty olefin metathesis products are insect pheromones. Pheromone compositions and methods of using them are also described.

An object of the present invention is to provide a novel method for producing a fluorine-containing methylene compound.

The above object can be achieved by a method for producing a compound represented by formula (1):

##STR00001## wherein R.sup.1 represents an organic group, R.sup.A represents hydrogen or fluorine, R.sup.4a represents hydrogen or an organic group, R.sup.4b represents hydrogen or an organic group, R.sup.5a represents hydrogen or an organic group, R.sup.5b represents hydrogen or an organic group, and R.sup.2 represents hydrogen or an organic group; R.sup.2 is optionally connected to R.sup.4a to form a ring; the method comprising step A of reacting a compound represented by formula (2):

##STR00002## wherein X.sup.1 represents a leaving group, and other symbols are as defined above, with a compound represented by formula (3):

##STR00003## wherein X.sup.2 represents a leaving group, and other symbols are as defined above, in the presence of a reducing agent as desired, under light irradiation.

An object of the present invention is to provide a novel method for producing a fluorine-containing methylene compound.

The above object can be achieved by a method for producing a compound represented by formula (1):

##STR00001## wherein R.sup.1 represents an organic group, R.sup.A represents hydrogen or fluorine, R.sup.4a represents hydrogen or an organic group, R.sup.4b represents hydrogen or an organic group, R.sup.5a represents hydrogen or an organic group, R.sup.5b represents hydrogen or an organic group, and R.sup.2 represents hydrogen or an organic group; R.sup.2 is optionally connected to R.sup.4a to form a ring; the method comprising step A of reacting a compound represented by formula (2):

##STR00002## wherein X.sup.1 represents a leaving group, and other symbols are as defined above, with a compound represented by formula (3):

##STR00003## wherein X.sup.2 represents a leaving group, and other symbols are as defined above, in the presence of a reducing agent as desired, under light irradiation.

Provided is a calixarene compound represented by structural formula (1). In structural formula (1), R.sup.1 and R.sup.2 each independently represent a structural moiety (A) having a functional group (I), a structural moiety (B) having a functional group (II) having a carbon-carbon unsaturated bond (excluding maleate groups), a structural moiety (C) having both the functional group (I) and the functional group (II), a monovalent organic group (D) that has 1 to 20 carbon atoms and is other than the structural moieties (A), (B) and (C), or a hydrogen atom (E). At least one of a plurality of R.sup.2s is the structural moiety (A), the structural moiety (B), the structural moiety (C), or the organic group (D).

##STR00001##

Provided is a calixarene compound represented by structural formula (1). In structural formula (1), R.sup.1 and R.sup.2 each independently represent a structural moiety (A) having a functional group (I), a structural moiety (B) having a functional group (II) having a carbon-carbon unsaturated bond (excluding maleate groups), a structural moiety (C) having both the functional group (I) and the functional group (II), a monovalent organic group (D) that has 1 to 20 carbon atoms and is other than the structural moieties (A), (B) and (C), or a hydrogen atom (E). At least one of a plurality of R.sup.2s is the structural moiety (A), the structural moiety (B), the structural moiety (C), or the organic group (D).

##STR00001##

A lubricity modifier for fuels contain a dicarboxylic acid monoester compound represented by formula (I). In formula (I), R.sub.1 represents a single bond, a substituted or unsubstituted C.sub.2-6 divalent alkenyl group, or a group having a structure of —R.sub.3—R.sub.4—R.sub.5—; R.sub.2 represents a substituted or unsubstituted C.sub.1-40 hydrocarbyl group; R.sub.3 and R.sub.5 each independently represents a single bond, or a substituted or unsubstituted C.sub.1-3 divalent alkyl group; and R.sub.4 represents a substituted or unsubstituted C.sub.3-12 divalent alicyclic group.

##STR00001##

A lubricity modifier for fuels contain a dicarboxylic acid monoester compound represented by formula (I). In formula (I), R.sub.1 represents a single bond, a substituted or unsubstituted C.sub.2-6 divalent alkenyl group, or a group having a structure of —R.sub.3—R.sub.4—R.sub.5—; R.sub.2 represents a substituted or unsubstituted C.sub.1-40 hydrocarbyl group; R.sub.3 and R.sub.5 each independently represents a single bond, or a substituted or unsubstituted C.sub.1-3 divalent alkyl group; and R.sub.4 represents a substituted or unsubstituted C.sub.3-12 divalent alicyclic group.

##STR00001##