Fluorocompound having highly fluorinated norbornane structure, fluoropolymer, and their production processes

A compound represented by the following formula (1A-1):

• wherein the symbols in the formula have the following meanings:
• Z:
• —CH(—OC(O)CT1═CH2)— or —CF(—CH2OC(O)CT1═CH2)— (wherein T1 is a hydrogen atom, a fluorine atom, a methyl group or a trifluoromethyl group);
• W1 and W2:
• each of them is independently a fluorine atom or a trifluoromethyl group;
• and
• R1, R2, R3 and R4:
• each of them is independently a fluorine atom or a C1-16 perfluoroalkyl group.

A process for producing a compound represented by the following formula (1), which comprises reacting a compound represented by the following formula (2) with a compound represented by CH2═CTC(O)J:

• wherein the symbols in the formulae have the following meanings:
• YA, YB, YC, YD, and YE:
• each of them is independently —CH(—OH)—, —CF(CH2OH)— or —CRARB—, provided that at least one of YA to YE is —CH(—OH)— or —CF(CH2OH)—, and at least one of YA to YE is —CRARB—;
• and
• ZA, ZB, ZC, ZD, and ZE:
• each of them is independently —CH(—OC(O)CT═CH2)—, —CF(—CH2OC(O)CT═CH2)— or —CRARB—, provided that at least one of ZA to ZE is —CH(—OC(O)CT═CH2)— or —CF(—CH2OC(O)CT═CH2)—, and at least one of ZA to ZE is —CRARB—;
• wherein YA corresponds to ZA, YB to ZB, YC to ZC, YD to ZD and YE to ZE, respectively;
• when each of ZA to ZE is —CH(—OC(O)CT═CH2)—, each of YA to YE is —CH(—OH)—;
• when each of ZA to ZE is —CF(—CH2OC(O)CT═CH2)—, each of YA to YE is —CF(CH2OH)—;
• and when each of ZA to ZE is —CRARB—, each of YA to YE is —CRARB—;
• each of RA and RB is independently a fluorine atom, a C1-16 perfluoroalkyl group or a C1-16 perfluoroalkyl group containing an etheric oxygen atom;
• and T is a hydrogen atom, a fluorine atom, a C1-3 alkyl group or a C1-3 fluoroalkyl group;
• WA and WB:
• each of them is independently a fluorine atom, a C1-16 perfluoroalkyl group or a C1-16 perfluoroalkyl group containing an etheric oxygen atom;
• J:
• a halogen atom;
• and
• n:
• 0, 1 or 2.

A compound represented by the following formula (2):

• wherein the symbols in the formula have the following meanings:
• YA, YB, YC, YD, and YE:
• each of them is independently —CH(—OH)—, —CF(CH2OH)— or —CRARB—, provided that at least one of YA to YE is —CH(—OH)— or —CF(CH2OH)—, and at least one of YA to YE is —CRARB— (wherein each of RA and RB is independently a fluorine atom, a C1-16 perfluoroalkyl group or a C1-16 perfluoroalkyl group containing an etheric oxygen atom);
• WA and WB:
• each of them is independently a fluorine atom, a C1-16 perfluoroalkyl group or a C1-16 perfluoroalkyl group containing an etheric oxygen atom;
• and
• n:
• 0, 1 or 2.

A compound represented by the following formula (2A-1):

• wherein the symbols in the formula have the following meanings:
• Y:
• —CH(—OH)— or —CF(—CH2OH)—;
• R1, R2, R3 and R4:
• each of them is independently a fluorine atom or a C1-16 perfluoroalkyl group;
• and
• W1 and W2:
• each of them is independently a fluorine atom or a trifluoromethyl group.

A process for producing a compound represented by the following formula (2), which comprises subjecting a compound represented by the following formula (3) to a reduction reaction:

• wherein the symbols in the formulae have the following meanings:
• XA, XB, XC, XD and XE:
• each of them is independently —C(O)—, —CF(C(O)G)- or —CRARB—, provided that at least one of XA to XE is —C(O)— or —CF(—C(O)G)- , and at least one of XA to XE is —CRARB—;
• YA, YB, YC, YD, and YE:
• each of them is independently —CH(—OH)—, —CF(CH2OH)— or —CRARB—, provided that at least one of YA to YE is —CH(—OH)— or —CF(CH2OH)—, and at least one of YA to YE is —CRARB—;
• wherein XA corresponds to YA, XB to YB, XC to YC, XD to YD and XE to YE, respectively;
• when each of YA to YE is —CH(—OH)—, each of XA to XD is —C(O)—;
• when each of YA to YE is —CF(—CH2OH)—, each of XA to XD is —CF(—C(O)G)-;
• and when each of YA to YE is —CRARB—, each of XA to XD is —CRARB—;
• each of RA and RB is independently a fluorine atom, a C1-16 perfluoroalkyl group or a C1-16 perfluoroalkyl group containing an etheric oxygen atom;
• G is a halogen atom or a C1-10 alkoxy group;
• WA and WB:
• each of them is independently a fluorine atom, a C1-16 perfluoroalkyl group or a C1-16 perfluoroalkyl group containing an etheric oxygen atom;
• and
• n:
• 0, 1 or 2.