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ChemInform Abstract: Cycloaromatization of a Non-Conjugated Polyenyne System: Synthesis of 5H-Benzo(d)fluoreno(3,2-b)pyrans via Diradicals Generated from 1-(2-(4- (2-Alkoxymethylphenyl)butan-1,3-diynyl))phenylpentan-2,4-diyn-1-ols and Trapping Evidence for the 1,2-Didehydrobenzene Diradical.

✍ Scribed by K. MIYAWAKI; R. SUZUKI; T. KAWANO; I. UEDA


Publisher
John Wiley and Sons
Year
2010
Weight
34 KB
Volume
28
Category
Article
ISSN
0931-7597

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✦ Synopsis


Cycloaromatization of a Non-Conjugated Polyenyne System: Synthesis of 5H-Benzo(d)fluoreno(3,2-b)pyrans via Diradicals Generated from 1-(2-(4-(2-Alkoxymethylphenyl)butan-1,3diynyl))phenylpentan-2,4-diyn-1-ols and Trapping Evidence for the 1,2-Didehydrobenzene Diradical.

-Mild thermolysis of the tetraynes (I) results in cyclization to the 5H-fluorenol derivatives (II) and (III). Similar thermolysis of (IV) in benzene gives the Diels-Alder product (VII), indicating an intermediate 1,2-didehydrobenzene diradical. These diradical is efficiently trapped by anthracene.

-(MIYAWAKI, K.; SUZUKI, R.;