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Reactions of dehydrobenzene II. 7,8-Benzobicyclo-[4.2.1]nona-2,4,7-trien-9-one; a 1,6-cycloaddition product of dehydrobenzene

✍ Scribed by T. Miwa; M. Kato; T. Tamano

Publisher: Elsevier Science
Year: 1969
Tongue: French
Weight: 207 KB
Volume: 10
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)88005-9

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✦ Synopsis

In a previous communication, we described the first example of l,&cycloaddition reaction of dehydrobenzene(1).

In this communication we report another example of this type of reaction.

In 1967, Ciabattoni, Crowley and Kende described the isolation of 6,7benzobicyclo[3.2.2]nona-3,6,8-trien-2-one (I) from the reaction mixture of tropone and benzyne (2). Ne examined this reaction to search for 1,6rcycloaddition product(s) of dehydrobenzene and isolated, in addition to the main product I, an isomer having a novel ring system, 7,8-benzobicyclo[4.2.llnona-2,4,7-trien+-one (II), as follows.

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