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Photochemical transformations of 2-methylene-bicyclo[3.2.2]Nona-3,6,8-triene. (Methylenehomobarrelene).

✍ Scribed by Zeev Goldschmidt; A. Worchel

Publisher: Elsevier Science
Year: 1973
Tongue: French
Weight: 108 KB
Volume: 14
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)86988-4

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✦ Synopsis

Current theoretical developments concerning the topological aspects of aromaticity in polycyclic hydrocarbons' prompts us to report a facile and synthetically useful preparation of two representatives of these systems, the barbaralyl (l_) and bishomotropylium (1) cations 2'3, by a photochemical synthesis of their hydrocarbon precursors. 1 2 -Thus, the acetone-sensitized photolysis4 of 2-methylene-bicyclo[3.2.2]nona-3,6,8-triene (2): readily prepared in 80% yield by the Wittig reaction of ketone 46 with methylenetriphenylphosphorane, resulted in the rapid disappearance of 2with concomitant formation of ca. 1:l mixture of two isomeric products 5 and 1 in practically quantitative yield. Separation was best effected _) by preparative glpc.'

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