1997•Journal of Heterocyclic ChemistryRequires access

Synthesis of new type benzo[b]thiophene fused quinones and their tetracyanoquinodimethane derivatives

Yoshihiro Ohba, Yasuo Murakami, Tyo Sone, Hiroshi Awano

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Abstract

Abstract A series of new type of benzo[b]thiophene‐fused 1,4‐benzoquinones and their tetracyanoquinodimethane derivatives were synthesized. The cyclic voltammetric data of new type quinones and tetracyanoquinodimethane derivatives displayed different behavior. All new quinones exhibit two reduction waves corresponding to the radical anion and dianion. On the other hand, most tetracyanoquinodimethane derivatives display a singlewave reduction to the dianion. The benzo[b]thiophene moiety fused tetracyanoquinodimethane derivatives reveal more negative reduction potentials than that of tetracyanoquinodimethane.

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Abstract A series of new type of benzo[b]thiophene‐fused 1,4‐benzoquinones and their tetracyanoquinodimethane derivatives were synthesized. The cyclic voltammetric data of new type quinones and tetracyanoquinodimethane derivatives displayed different behavior. All new quinones exhibit two reduction waves corresponding to the radical anion and dianion. On the other hand, most tetracyanoquinodimethane derivatives display a singlewave reduction to the dianion. The benzo[b]thiophene moiety fused tetracyanoquinodimethane derivatives reveal more negative reduction potentials than that of tetracyanoquinodimethane.

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Available abstract

Abstract A series of new type of benzo[b]thiophene‐fused 1,4‐benzoquinones and their tetracyanoquinodimethane derivatives were synthesized. The cyclic voltammetric data of new type quinones and tetracyanoquinodimethane derivatives displayed different behavior. All new quinones exhibit two reduction waves corresponding to the radical anion and dianion. On the other hand, most tetracyanoquinodimethane derivatives display a singlewave reduction to the dianion. The benzo[b]thiophene moiety fused tetracyanoquinodimethane derivatives reveal more negative reduction potentials than that of tetracyanoquinodimethane.

Key concepts: Tetracyanoquinodimethane, Chemistry, Thiophene, Moiety, Medicinal chemistry, Cyclic voltammetry, Stereochemistry, Photochemistry

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