Tetrahedron p. 5081 - 5088 (1986)
Update date:2022-08-04
Topics:
Malomidou-Xenikaki, E.
Nicolaides, D. N.
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 phenylhydrozyne 12.The acetyl derivatives 8 and 15 of propellanes 7 and 14 are also prepared and studied.
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Doi:10.1021/ja200130h
(2011)Doi:10.1016/S0040-4039(00)84888-1
(1986)Doi:10.1080/15257779408013207
(1994)Doi:10.1002/chem.201100458
(2011)Doi:10.1021/jo801898g
(2008)Doi:10.1002/ardp.19532860902
(1953)
