Reactivity of [1]Benzothieno[3,2-b][1]benzothiophene - Electrophilic and Metallation Reactions

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Title:Reactivity of [1]Benzothieno[3,2-b][1]benzothiophene - Electrophilic and Metallation Reactions
Creators:
Košata, Bedřich
Kozmík, Václav
Svoboda, Jiří
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 67, 5, pp. 645-664
Uncontrolled Keywords:Liquid crystals, Regioselectivity, [1]Benzothieno[3,2-<i>b</i>][1]benzothiophene, Metallation, Formylation, Nitration, Acetylation, Electrophilic substitution

Abstract

Electrophilic nitration, formylation and acetylation of the title heterocycle <strong>1</strong> were studied. Monosubstitution proceeds preferentially in position 2 and to a lesser extent in position 4. Lowering the reaction temperature substantially increases regioselectivity of nitration and acetylation. Substitution reactions of the 2-substituted derivatives of <strong>1</strong> led to the corresponding 2,7-disubstituted derivatives as major products. Formation of other regioisomers was also observed. Metallation of <strong>1</strong> with butyllithium preferably proceeds in position 1; subsequent reaction with <i>N</i>,<i>N</i>-dimethylformamide, carbon dioxide or iodine gives rise to corresponding 1-substituted derivatives. Long-chain 2,7-disubstitued derivatives exhibit liquid-crystalline properties. <p>

Title:Reactivity of [1]Benzothieno[3,2-b][1]benzothiophene - Electrophilic and Metallation Reactions
Creators:
Košata, Bedřich
Kozmík, Václav
Svoboda, Jiří
Uncontrolled Keywords:Liquid crystals, Regioselectivity, [1]Benzothieno[3,2-<i>b</i>][1]benzothiophene, Metallation, Formylation, Nitration, Acetylation, Electrophilic substitution
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:67
Number:5
Page Range:pp. 645-664
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20020645UNSPECIFIED
ID Code:1948
Item Type:Article
Deposited On:06 Feb 2009 17:14
Last Modified:06 Feb 2009 16:14

Citation

Košata, Bedřich; Kozmík, Václav; Svoboda, Jiří (2002) Reactivity of [1]Benzothieno[3,2-b][1]benzothiophene - Electrophilic and Metallation Reactions. Collection of Czechoslovak Chemical Communications, 67 (5). pp. 645-664. ISSN 0010-0765

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