Journal of the Chemical Society. Chemical communications p. 1637 - 1639 (1989)
Update date:2022-08-02
Topics:
Barlow, Michael G.
Tajammal, Sabiha
Tipping, Anthony E.
Reaction of furan with the dialkynyl ester (CF3C<*>C)2CPhOCOPh (1a) in dichloromethane at 50 deg C affords a mixture of four 1:1 adducts, the (Z)-isomer of triene (4a) (major product), diketone (5a), and benzopentacyclononenes (3) and (6), via the common intermediate 2-benzoyloxy-2-phenyl-4,10-bis(trifluoromethyl)-7-oxapentacyclo<4.4.0.0 1,3 .0 5,9 .0 8,10 >dec-3-ene (9) formed from the bis Diels-Alder adduct by intramolecular ( ? 2 s + ? 2 s + ? 2 s ) cycloaddition followed by retro-cleavage of furan; the corresponding reaction with the ester (CF3C<*>C)2CMeOCOMe (1b) gives analogously diketone (5b) (major product) and a mixture of the (E)- and (Z)-isomers of triene (4b), a rearranged furan-dialkyne 2:1 adduct (7) or (8) also being formed.
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