3,4-dioxythiophene derivatives

1. A process for producing compounds represented by the following formula (I),

wherein,

A, B, C and D in each case independently denote a member selected from the group consisting of a bond, alkylene, substituted alkylene, cycloalkylene, substituted cycloalkylene, arylene, substituted arylene and (—O—(CR 1 R 2 ) m ) x ,

wherein R 1 and R 2 in each case are independently selected from the group consisting of hydrogen, alkyl, and substituted alkyl,

m is an integer from 1 to 10 and

x is an integer from 1 to 10,

provided that at least one of the units A, B, C or D is other than a bond, said process comprising,

(i) reacting a compound represented by the following formula (II),

TosO-A-B-C-D-OTos  (II)

wherein

A, B, C and D are each as described with regard to formula (I), and

Tos denotes a member selected from the group consisting of p-toluenesulfonyl and trifluoromethanesulfonyl,

with a thiophene represented by the following formula (III),

wherein,

R denotes C 1 –C 18 alkyl, and

m denotes H, Li, Na or K,

thereby forming an intermediate 3,4-dioxythiophene diester,

(ii) saponifying the intermediate 3,4-dioxythiophene diester, thereby forming an intermediate 3,4-dioxythiophene dicarboxylic acid, and

(iii) decarboxylating said intermediate 3,4-dioxythiophene dicarboxylic acid, thereby forming the compound represented by formula (I).

2. The process of claim 1 wherein A, B, C and D together jointly denote

—(CR 3 R 4 ) n —(CH 2 ) o —(CR 5 R 6 ) p —

or

—(CH 2 ) q —(CR 7 R 8 ) r —(CH 2 ) s —,

wherein R 3 , R 4 , R 5 , R 6 , R 7 and R 8 in each case independently denote a member selected from the group consisting of hydrogen, halogen, C 1 –C 10 alkyl and substituted C 1 –C 10 alkyl, and n, o, p, q, r and s in each case independently denote an integer from 1 to 10.

3. The process of claim 1 wherein A, B, C and D together jointly denote a C 6 –C 8 cycloalkylene.

4. The process of claim 1 wherein A, B, C and D together jointly denote a unit represented by the following formula (IV),

wherein,

t and u in each case independently denote an integer from 0 to 5, and further aromatic ring systems may be fused onto the phenyl rings.

5. The process of claim 1 wherein A, B, C and D jointly denote

—((CH 2 ) v —X—) y —Ar—(X—(CH 2 ) w ) z —,

wherein

X is a bond or oxygen and

Ar denotes a member selected from the group consisting of phenylene, substituted phenylene, naphthylene and substituted naphthylene,

v and w in each case independently denote an integer from 1 to 5, and

y and z in each case independently denote an integer from 1 to 10.

6. The process of claim 1 wherein A, B, C and D together jointly denote,

—((CR 9 R 10 ) a —O) b —(CR 11 R 12 ) c —,

wherein R 9 , R 10 , R 11 and R 12 in each case independently denote a member selected from the group consisting of hydrogen, C 1 –C 10 alkyl and substituted C 1 –C 10 alkyl, a and c in each case independently denote an integer from 1 to 10, and b denotes an integer from 1 to 8.

7. The process of claim 1 wherein R denotes a member selected from the group consisting of methyl, ethyl and n-propyl.

8. A compound represented the following formula (I),

wherein,

A, B, C and D together jointly denote a unit of the formula (IV),

wherein,

t and u in each case independently denote an integer from 0 to 5, and further aromatic ring systems may be fused onto the phenyl rings.

9. A compound represented by the following formula (I),

wherein,

A, B, C and D together jointly denote

—((CH 2 ) v —X—) y —Ar—(X—(CH 2 ) w ) z —,

wherein,

X denotes a bond or oxygen and

Ar denotes a member selected from the group consisting essentially of phenylene, substituted phenylene, naphthylene and substituted naphthylene,

v and w in each case independently denote an integer from 1 to 5, and

y and z in each case independently denote an integer from 1 to 10.