Add time:08/02/2019 Source:sciencedirect.com
5-Ethoxycarbonylmethylene-cyclooctanone (3) is prepared by Wittig monoolefination of dione 1 with phosphorus ylide 2. Thermal transannular cyclization of oxime 6 and phenylhydrazone 12 of the ketone 3 affords 3-oxa-2-aza- and 2,3-diaza[3.3.3] propellanes 7 and 14 respectively. Irradiation of ketone 3, its oxime 9, and its dimethylhydrazone 16 furnish 9-oxa-, and 9-aza[3.3.2] propellanes 11, 10, and 17, respectively. In addition to the propellane 14, phenylazobicyclo compound 13 is also obtained from phenylhydrazone 12. The acetyl derivatives 8 and 15 of propellanes 7 and 14 are also prepared and studied.
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