3,4-dioxythiophene derivatives

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

Reexamination Certificate

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Reexamination Certificate

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11011515

ABSTRACT:
A process for the production of 3,4-dioxythiophene compounds represented by the following formula (I),is described. In formula (I) A, B, C and D in each case independently denote a bond, optionally substituted alkylene, optionally substituted cycloalkylene, optionally substituted arylene or (O—(CR1R2)m)x, where R1and R2in each case mutually independently denote hydrogen or optionally substituted alkyl, m denotes an integer from 1 to 10 and x denotes an integer from 1 to 10, provided that at least one of the units A, B, C or D does not denote a bond. The process involves reacting a 3,4-dihydroxythiophene or the alkali metal salt thereof with the following compound,in-line-formulae description="In-line Formulae" end="lead"?TosO-A-B-C-D-OTos,in-line-formulae description="In-line Formulae" end="tail"?thus forming an intermediate 3,4-dioxythiophene diester. The intermediate 3,4-dioxythiophene diester is saponified, thus forming an intermediate 3,4-dioxythiophene dicarboxylic acid, which is then decarboxylated, thereby forming the 3,4-dioxythiophene compound represented by formula-(I).

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T. Sone et al: “Synthesis and reductive desulfurization of crown ethers containing thiophene subunit” Bulletin of the Chemical Society of Japan, Bd. 62, Nr. 3, 1989, Seiten 838-844, XP002317503.

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