Isomerization of cyclohexenedicarboxylic acid and its derivatives

A compound of Formula (I):

• wherein
• R1 is H or C1-6 alkyl;
• R2 is H or C1-6 alkyl;
• and
• each R3 is independently selected from the group consisting of H, C1-20 alkyl, aryl, carborane, heteroaryl, heterocyclyl, C1-20 alkyl-O—Zn—O—C1-20 alkyl, C1-20 alkyl-O—Zn—O-heteroaryl, heteroaryl-O—Zn—O-heteroaryl, C1-20 alkyl-O—Zn—O-heterocyclyl, heterocyclyl-O—Zn—O-heterocyclyl, heterocyclyl-O—Zn—O-heteroaryl, —P(O)(R6)2, —P(O)(OR5)2, —C1-6 alkylene-P(O)(R6)2, and —C1-6 alkylene-P(O)(OR5)2, wherein C1-20 alkyl, heteroaryl, and heterocyclyl can be optionally substituted 1 to 3 times with R4;
• R4 is selected from the group consisting of H, C1-6 alkyl, SH, NH2, PH2, P(O)(OR5)2, P(O)(OR5)3, P(O)(OR5)2R6, P(O)(OR5)(R6)2, P(O)(R6)2, BH2,
• a is 1, 2, 3, or 4;
• b is 1, 2, or 3;
• c is 1, 2, 3, 4, or 5;
• each R5 is independently selected from the group consisting of H, C1-6 alkyl, C1-6 alkenyl, and aryl, wherein aryl can be optionally substituted 1 to 3 times with halogen, or C1-6 alkyl;
• each R6 is independently selected from the group consisting of H, C1-6 alkyl, C1-6 alkenyl, and aryl, wherein aryl can be optionally substituted 1 to 3 times with halogen, or C1-6 alkyl,
• is the point of attachment of R4 to R3;
• or a salt thereof.

A process of making a polymer of Formula (V):

• wherein
• Y is NH or O;
• R is independently selected from the group consisting of H and C1-20 alkyl;
• each R3 is independently selected from the group consisting of H, C1-20 alkyl, aryl, carborane, heteroaryl, heterocyclyl, C1-20 alkyl-O—Zn—O—C1-20 alkyl, C1-20 alkyl-O—Zn—O-heteroaryl, heteroaryl-O—Zn—O-heteroaryl, C1-20 alkyl-O—Zn—O-heterocyclyl, heterocyclyl-O—Zn—O-heterocyclyl, heterocyclyl-O—Zn—O-heteroaryl, —P(O)(R6)2, —P(O)(OR5)2, —C1-6 alkylene-P(O)(R6)2, and —C1-6 alkylene-P(O)(OR5)2, wherein C1-20 alkyl, heteroaryl, and heterocyclyl can be optionally substituted 1 to 3 times with R4;
• R4 is selected from the group consisting of H, C1-6 alkyl, SH, NH2, PH2, P(O)(OR5)2, P(O)(OR5)3, P(O)(OR5)2R6, P(O)(OR5)(R6)2, P(O)(R6)2, BH2,
• a is 1, 2, 3, or 4;
• b is 1, 2, or 3;
• c is 1, 2, 3, 4, or 5;
• each R5 is independently selected from the group consisting of H, C1-6 alkyl, C1-6 alkenyl, and aryl, wherein aryl can be optionally substituted 1 to 3 times with halogen, or C1-6 alkyl;
• each R6 is independently selected from the group consisting of H, C1-6 alkyl, C1-6 alkenyl, and aryl, wherein aryl can be optionally substituted 1 to 3 times with halogen, or C1-6 alkyl,
• is the point of attachment of R4 to R3;
• i is 1 to 1,000,000;
• j is 1 to 1,000,000;
• m is 0 to 32;
• s is 0 to 32;
• and
• is a terminal group of the polymer;
• is a single or a double bond, with only one being a double bond, said process comprising:
• providing a compound having the structure of Formula (I):
• or a salt thereof,
• providing a compound having the structure of Formula (VI):
• providing a compound having the structure of Formula (VII):
• and
• reacting the compound of Formula (I), the compound of Formula (VI), and the compound of Formula (VII) under conditions effective to produce the polymer of Formula (V).

A polymer of Formula (V):

• wherein
• Y is NH or O;
• R is independently selected from the group consisting of H and C1-20 alkyl;
• each R3 is independently selected from the group consisting of H, C1-20 alkyl, aryl, carborane, heteroaryl, heterocyclyl, C1-20 alkyl-O—Zn—O—C1-20 alkyl, C1-20 alkyl-O—Zn—O-heteroaryl, heteroaryl-O—Zn—O-heteroaryl, C1-20 alkyl-O—Zn—O-heterocyclyl, heterocyclyl-O—Zn—O-heterocyclyl, heterocyclyl-O—Zn—O-heteroaryl, —P(O)(R6)2, —P(O)(OR5)2, —C1-6 alkylene-P(O)(R6)2, and —C1-6 alkylene-P(O)(OR5)2, wherein C1-20 alkyl, heteroaryl, and heterocyclyl can be optionally substituted 1 to 3 times with R4;
• R4 is selected from the group consisting of H, C1-6 alkyl, SH, NH2, PH2, P(O)(OR5)2, P(O)(OR5)3, P(O)(OR5)2R6, P(O)(OR5)(R6)2, P(O)(R6)2, BH2,
• a is 1, 2, 3, or 4;
• b is 1, 2, or 3;
• c is 1, 2, 3, 4, or 5;
• each R5 is independently selected from the group consisting of H, C1-6 alkyl, C1-6 alkenyl, and aryl, wherein aryl can be optionally substituted 1 to 3 times with halogen, or C1-6 alkyl;
• each R6 is independently selected from the group consisting of H, C1-6 alkyl, C1-6 alkenyl, and aryl, wherein aryl can be optionally substituted 1 to 3 times with halogen, or C1-6 alkyl,
• is the point of attachment of R4 to R3;
• i is 1 to 1,000,000;
• j is 1 to 1,000,000;
• m is 0 to 32;
• s is 0 to 32;
• and
• is a terminal group of the polymer;
• is a single or a double bond, with only one of being a double bond.