Nonconcerted cycloaddition reactions of fused 2-vinylthiophenes with dimethyl acetylenedicarboxylate.

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22310%2F05%3A00014085" target="_blank" >RIV/60461373:22310/05:00014085 - isvavai.cz</a>

Result on the web

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DOI - Digital Object Identifier

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Result language

angličtina

Original language name

Nonconcerted cycloaddition reactions of fused 2-vinylthiophenes with dimethyl acetylenedicarboxylate.

Original language description

As shown recently [1,2], fused polycyclic system of benzothieno[3,2-b]benzothiophene can serve successfully as a new type of core for design of antiferroelectric liquid crystals. Thus, our effort was focused on development of smart synthetic methods forpreparation if this core, e.g. by involving Diels-Alder reactions. However, in a preliminary study [3] we found, that cycloaddition reaction of 2-vinylthieno[3,2-b]benzothiophene with dimethyl acetylenedicarboxylate afforded a broad range of products. Among them compounds with a novel heterocyclic cyclopenta[5,6]thiopyrano[3,2-b][1]benzothiophene system were identified. Herein we report results of an exhaustive study of this cycloaddition reaction of various related vinylthiophene (and 2-vinylselenophene) 1 derivatives with dimethyl acetylenedicarboxylate. Based on the structure of isolated products and their distribution (only principal products are shown in Scheme 1), a nonconcerted mechanisms of the cycloaddition was postulated [2].

Czech name

Nonconcerted cycloaddition reactions of fused 2-vinylthiophenes with dimethyl acetylenedicarboxylate.

Czech description

As shown recently [1,2], fused polycyclic system of benzothieno[3,2-b]benzothiophene can serve successfully as a new type of core for design of antiferroelectric liquid crystals. Thus, our effort was focused on development of smart synthetic methods forpreparation if this core, e.g. by involving Diels-Alder reactions. However, in a preliminary study [3] we found, that cycloaddition reaction of 2-vinylthieno[3,2-b]benzothiophene with dimethyl acetylenedicarboxylate afforded a broad range of products. Among them compounds with a novel heterocyclic cyclopenta[5,6]thiopyrano[3,2-b][1]benzothiophene system were identified. Herein we report results of an exhaustive study of this cycloaddition reaction of various related vinylthiophene (and 2-vinylselenophene) 1 derivatives with dimethyl acetylenedicarboxylate. Based on the structure of isolated products and their distribution (only principal products are shown in Scheme 1), a nonconcerted mechanisms of the cycloaddition was postulated [2].

Type

O - Miscellaneous

CEP classification

CC - Organic chemistry

OECD FORD branch

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Project

<a href="/en/project/GA202%2F05%2F0431" target="_blank" >GA202/05/0431: Polar order in new liquid crystalline materials</a><br>

Continuities

Z - Vyzkumny zamer (s odkazem do CEZ)

Publication year

2005

Confidentiality

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů