The present invention provides an industrially applicable method for production of a fluorine-containing cyclopropane carboxylic acid compound useful as an intermediate for pharmaceutical and agrichemical products. A fluorine-containing cyclopropane monoester is obtained by: forming a fluorine-containing cyclic sulfate with the use of a fluorine-containing diol compound and sulfuryl fluoride (as a cyclic sulfuric esterification step); reacting the fluorine-containing cyclic sulfate with a malonic diester, thereby forming a fluorine-containing cyclopropane diester (as a cyclopropanation step); and hydrolyzing the fluorine-containing cyclopropane diester (as a hydrolysis step). The fluorine-containing cyclopropane carboxylic acid compound, such as fluorine-containing cyclopropane monoester or its salt, can be obtained with high chemical and optical purity by mixing the fluorine-containing cyclopropane monoester with an amine and subjecting the resulting salt of the fluorine-containing cyclopropane monoester and amine to recrystallization purification.

The present invention provides an industrially applicable method for production of a fluorine-containing cyclopropane carboxylic acid compound useful as an intermediate for pharmaceutical and agrichemical products. A fluorine-containing cyclopropane monoester is obtained by: forming a fluorine-containing cyclic sulfate with the use of a fluorine-containing diol compound and sulfuryl fluoride (as a cyclic sulfuric esterification step); reacting the fluorine-containing cyclic sulfate with a malonic diester, thereby forming a fluorine-containing cyclopropane diester (as a cyclopropanation step); and hydrolyzing the fluorine-containing cyclopropane diester (as a hydrolysis step). The fluorine-containing cyclopropane carboxylic acid compound, such as fluorine-containing cyclopropane monoester or its salt, can be obtained with high chemical and optical purity by mixing the fluorine-containing cyclopropane monoester with an amine and subjecting the resulting salt of the fluorine-containing cyclopropane monoester and amine to recrystallization purification.

Thionyl tetrafluoride gas reacts efficiently with primary amines to form reactive iminosulfur oxydifluoride compounds. These dual S.sup.VIF loaded iminosulfur oxydifluoride compounds, in turn, readily react with secondary amines or aryloxy silyl ethers (ArOSiR.sub.3), yielding the corresponding fused heteroatom-linked substrates. Iminosulfur oxyfluoride polymers also are provided by disclosed methods.

Thionyl tetrafluoride gas reacts efficiently with primary amines to form reactive iminosulfur oxydifluoride compounds. These dual S.sup.VIF loaded iminosulfur oxydifluoride compounds, in turn, readily react with secondary amines or aryloxy silyl ethers (ArOSiR.sub.3), yielding the corresponding fused heteroatom-linked substrates. Iminosulfur oxyfluoride polymers also are provided by disclosed methods.

Provided is a nonaqueous electrolyte solution for a lithium secondary battery, the nonaqueous electrolyte solution containing a compound (I) represented by Formula (I) and a compound (II) represented by Formula (II). In Formula (I), each of R.sup.1 and R.sup.2 independently represents a substituent such as an alkyl group having from 1 to 7 carbon atoms. In Formula (II), R.sup.3 represents an oxygen atom or the like; R.sup.4 represents a group represented by Formula (ii-1), a group represented by Formula (ii-2), or the like; and * represents a binding position. In Formula (ii-1), R.sup.41 represents an oxymethylene group or the like and, in Formula (ii-2), R.sup.42 represents an alkyl group having from 1 to 6 carbon atoms, or the like.

##STR00001##

Provided is a nonaqueous electrolyte solution for a lithium secondary battery, the nonaqueous electrolyte solution containing a compound (I) represented by Formula (I) and a compound (II) represented by Formula (II). In Formula (I), each of R.sup.1 and R.sup.2 independently represents a substituent such as an alkyl group having from 1 to 7 carbon atoms. In Formula (II), R.sup.3 represents an oxygen atom or the like; R.sup.4 represents a group represented by Formula (ii-1), a group represented by Formula (ii-2), or the like; and * represents a binding position. In Formula (ii-1), R.sup.41 represents an oxymethylene group or the like and, in Formula (ii-2), R.sup.42 represents an alkyl group having from 1 to 6 carbon atoms, or the like.

##STR00001##

A non-aqueous electrolyte for a lithium-ion battery and a lithium-ion battery. The non-aqueous electrolyte comprises unsaturated phosphate compounds and unsaturated cyclic carboxylic acid anhydride compounds. The unsaturated phosphate compounds have the structure illustrated in structural formula 4; structural formula 4: R.sub.13, R.sub.11, and R.sub.12 are independently selected from hydrocarbon groups having 1-5 carbon atoms respectively, and at least one of R.sub.13, R.sub.11, and R.sub.12 is an unsaturated hydrocarbon group containing double bonds or triple bonds; the unsaturated cyclic carboxylic acid anhydride compounds have the structure illustrated in structural formula 5; structural formula 5: R.sub.14 is independently selected from vinylidene having 2-4 carbon atoms or fluoro-substituted vinylidene. By means of the synergistic effect of two compounds, the non-aqueous electrolyte has excellent high-temperature cycling performance and storage performance, and also has lower impedance and good low-temperature performance.

##STR00001##

A non-aqueous electrolyte for a lithium-ion battery and a lithium-ion battery. The non-aqueous electrolyte comprises unsaturated phosphate compounds and unsaturated cyclic carboxylic acid anhydride compounds. The unsaturated phosphate compounds have the structure illustrated in structural formula 4; structural formula 4: R.sub.13, R.sub.11, and R.sub.12 are independently selected from hydrocarbon groups having 1-5 carbon atoms respectively, and at least one of R.sub.13, R.sub.11, and R.sub.12 is an unsaturated hydrocarbon group containing double bonds or triple bonds; the unsaturated cyclic carboxylic acid anhydride compounds have the structure illustrated in structural formula 5; structural formula 5: R.sub.14 is independently selected from vinylidene having 2-4 carbon atoms or fluoro-substituted vinylidene. By means of the synergistic effect of two compounds, the non-aqueous electrolyte has excellent high-temperature cycling performance and storage performance, and also has lower impedance and good low-temperature performance.

##STR00001##

An electrolyte, electrochemical device, battery, capacitor, and/or the like include a salt; and a fluorinated organosulfate compound represented by Formula I:

##STR00001##

wherein, R.sup.1 is H, OR.sup.3, alkyl, alkenyl, alkynyl, aralkyl, or silyl; R.sup.2 is H, OR.sup.3, alkyl, alkenyl, alkynyl, aralkyl, or silyl; and R.sup.3 is H, alkyl, alkenyl, alkynyl, aryl, heterocyclyl, heteroaryl, or siloxy; or where R.sup.1 and R.sup.2 join together to form a cyclic compound incorporating the OS(O).sub.2O group; wherein at least one R.sup.1 and R.sup.2 is fluorinated.

An electrolyte, electrochemical device, battery, capacitor, and/or the like include a salt; and a fluorinated organosulfate compound represented by Formula I:

##STR00001##

wherein, R.sup.1 is H, OR.sup.3, alkyl, alkenyl, alkynyl, aralkyl, or silyl; R.sup.2 is H, OR.sup.3, alkyl, alkenyl, alkynyl, aralkyl, or silyl; and R.sup.3 is H, alkyl, alkenyl, alkynyl, aryl, heterocyclyl, heteroaryl, or siloxy; or where R.sup.1 and R.sup.2 join together to form a cyclic compound incorporating the OS(O).sub.2O group; wherein at least one R.sup.1 and R.sup.2 is fluorinated.