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Reactions of a novel benzyne annelated with two bicyclo[2.2.2]octene units

โœ Scribed by Akira Matsuura; Tohru Nishinaga; Koichi Komatsu

Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
280 KB
Volume
38
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

Anthmnilic acid 9 amI odibromobenzme 14 annelated with two bicyclo[2.2.2]octene units were synthesized as the precursors for titled benzyne 3. The generation of 3 was confkmed by trapping with forao and its derivative. In the absence of trapping agent, benzyne 3 generated by diamtization of 9 gave acridone 12 while that generated via lithiation of 14 dimerizcd to give BCOarmelated biphenylene 11. The HOMO level of 11 is considerably raised as shown by cyclic voltammetry. 0 1997 Elsevier Science Ltd.

Benzyne has been playing an important role as reactive intermediate in organic chemistry. Among its wide variety of reactions,1 cycloaddition is particularly useful for construction of additional carbon skeletons.

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