Tetrahedron p. 1567 - 1574 (1983)
Update date:2022-07-30
Topics:
Fadel, A.
Salauen, J.
Conia, J. M.
Cyclobutene, prepared by base-induced elimination from tosyloxycyclobutane 19 undergoes cycloaddition with ethyl propiolate in the presence of AlCl3 to provide ethyl bicyclo<2.2.0>hex-2-ene-2-carboxylate 20.This cycloadduct at room temperature and in the presence of AlCl3 undergoes forbidden ring opening into ethyl cyclohexa-1,3-diene-2-carboxylate 21.The cycloaddition of cyclobutene with dichloroketene provides 3,3-dichlorobicyclo<2.2.0>hexan-2-one 24 and after reductive halogen removal the endo 3-chloro bicyclo<2.2.0>hexan-2-one 28 (the first study of this strained system).However, further dechlorination of 28 results in rearrangement and fragmentation reactions.
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Doi:10.1016/0008-6215(83)88059-8
(1983)Doi:10.1016/j.jorganchem.2005.07.108
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(1984)
