The present invention is directed to certain semifluorinated compounds and to compositions comprising such compounds. The invention further provides the use of the compounds and of the compositions as medicaments for topical administration to the eye.

The present invention is directed to certain semifluorinated compounds and to compositions comprising such compounds. The invention further provides the use of the compounds and of the compositions as medicaments for topical administration to the eye.

The present invention is directed to certain semifluorinated compounds and to compositions comprising such compounds. The invention further provides the use of the compounds and of the compositions as medicaments for topical administration to the eye.

The present invention is directed to certain semifluorinated compounds and to compositions comprising such compounds. The invention further provides the use of the compounds and of the compositions as medicaments for topical administration to the eye.

This method for producing a fullerene derivative is a method for producing a fullerene derivative having a partial structure shown by formula (1) by reacting a predetermined halogenated compound and two carbon atoms adjacent to each other for forming a fullerene skeleton in a mixed solvent of an aromatic solvent and an aprotic polar solvent having a C═O or S═O bond in the presence of at least one metal selected from the group comprising manganese, iron, and zinc; ##STR00001##
(in formula (1), C* are each carbon atoms adjacent to each other for forming a fullerene skeleton, A is a linking group having 1-4 carbon atoms for forming a ring structure with two C*, in which a portion thereof may be a substituted or condensed group).

This method for producing a fullerene derivative is a method for producing a fullerene derivative having a partial structure shown by formula (1) by reacting a predetermined halogenated compound and two carbon atoms adjacent to each other for forming a fullerene skeleton in a mixed solvent of an aromatic solvent and an aprotic polar solvent having a C═O or S═O bond in the presence of at least one metal selected from the group comprising manganese, iron, and zinc; ##STR00001##
(in formula (1), C* are each carbon atoms adjacent to each other for forming a fullerene skeleton, A is a linking group having 1-4 carbon atoms for forming a ring structure with two C*, in which a portion thereof may be a substituted or condensed group).

An object of the present invention is to provide a simple, low-cost, and industrial method of producing a compound having a polyene skeleton containing hydrogen and fluorine and/or chlorine. A method of producing a halogenated diene represented by formula (1): A.sup.1A.sup.2C═CA.sup.3-CA.sup.4=CA.sup.5A.sup.6 [A.sup.1, A.sup.2, A.sup.5, and A.sup.6 are each independently hydrogen, fluorine, chlorine, a (perfluoro)alkyl group having 1 to 3 carbon atoms, or a (perfluoro)alkenyl group; A.sup.3 and A.sup.4 are each independently hydrogen, fluorine, or chlorine; at least one of A.sup.1 to A.sup.6 is hydrogen; at least one of A.sup.1 to A.sup.6 is fluorine or chlorine] comprises a step of subjecting the same or different halogenated olefin(s) represented by formula (2): A.sup.7A.sup.8C═CA.sup.9X [A.sup.7 and A.sup.8 are each independently hydrogen, fluorine, chlorine, a (perfluoro)alkyl group having 1 to 3 carbon atoms, or a (perfluoro)alkenyl group; A.sup.9 is each independently hydrogen, fluorine, or chlorine; X is bromine or iodine] to a coupling reaction in the presence of a zero-valent metal and a metal salt.

An object of the present invention is to provide a simple, low-cost, and industrial method of producing a compound having a polyene skeleton containing hydrogen and fluorine and/or chlorine. A method of producing a halogenated diene represented by formula (1): A.sup.1A.sup.2C═CA.sup.3-CA.sup.4=CA.sup.5A.sup.6 [A.sup.1, A.sup.2, A.sup.5, and A.sup.6 are each independently hydrogen, fluorine, chlorine, a (perfluoro)alkyl group having 1 to 3 carbon atoms, or a (perfluoro)alkenyl group; A.sup.3 and A.sup.4 are each independently hydrogen, fluorine, or chlorine; at least one of A.sup.1 to A.sup.6 is hydrogen; at least one of A.sup.1 to A.sup.6 is fluorine or chlorine] comprises a step of subjecting the same or different halogenated olefin(s) represented by formula (2): A.sup.7A.sup.8C═CA.sup.9X [A.sup.7 and A.sup.8 are each independently hydrogen, fluorine, chlorine, a (perfluoro)alkyl group having 1 to 3 carbon atoms, or a (perfluoro)alkenyl group; A.sup.9 is each independently hydrogen, fluorine, or chlorine; X is bromine or iodine] to a coupling reaction in the presence of a zero-valent metal and a metal salt.

An object of the present invention is to provide a simple, low-cost, and industrial method of producing a compound having a polyene skeleton containing hydrogen and fluorine and/or chlorine. A method of producing a halogenated diene represented by formula (1): A.sup.1A.sup.2C═CA.sup.3-CA.sup.4=CA.sup.5A.sup.6 [A.sup.1, A.sup.2, A.sup.5, and A.sup.6 are each independently hydrogen, fluorine, chlorine, a (perfluoro)alkyl group having 1 to 3 carbon atoms, or a (perfluoro)alkenyl group; A.sup.3 and A.sup.4 are each independently hydrogen, fluorine, or chlorine; at least one of A.sup.1 to A.sup.6 is hydrogen; at least one of A.sup.1 to A.sup.6 is fluorine or chlorine] comprises a step of subjecting the same or different halogenated olefin(s) represented by formula (2): A.sup.7A.sup.8C═CA.sup.9X [A.sup.7 and A.sup.8 are each independently hydrogen, fluorine, chlorine, a (perfluoro)alkyl group having 1 to 3 carbon atoms, or a (perfluoro)alkenyl group; A.sup.9 is each independently hydrogen, fluorine, or chlorine; X is bromine or iodine] to a coupling reaction in the presence of a zero-valent metal and a metal salt.

Provided is a method for producing (alkyl)arene compounds represented by Formulae 3-1, 3-2, and 3-3 by the Friedel-Crafts alkylation reaction of alkyl halide compounds and arene compounds using organic phosphine compounds as a catalyst.

##STR00001##