- Stepwise mechanisms in cyclopropylcarbene reactions
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Decomposition of a naphtho-fused cyclopropyldiazomethane leads to benzocyclooctatetraene, 1-vinylnaphthalene, 2-vinylnaphthalene, and small amounts of benzobarrelene. Diradical intermediates are postulated.
- Cummins, Jordan M.,Porter, Timothy A.,Jones Jr., Maitland
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p. 6473 - 6476
(2007/10/03)
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- Synthesis, Reactions and Thermal Properties of endo-5,12:endo-6,11-Dietheno-5,5a,6,11,11a,12-hexahydronaphthacene
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The title compound 6 was synthesized in nine steps, starting from the Diels-Alder adduct 21 of ketomethanoethanonaphthalene 20 and p-benzoquinone, via 7,8-dimethylidenediethenoanthracene 10 followed by Diels-Alder reaction with (E)-bis(phenylsulfonyl)ethylene and aromatization.Photocyclization of 6 led to 32 via an intramolecular cycloaddition.Hydrogenation and epoxidation of 6 gave the corresponding bis-benzo hydrocarbon 33 and bis-epoxide 34.Bromination of 6 proceeded by transannular reaction to produce N-type exo, endo dibromide 35b and U-type exo, exo dibromide 36b.Compound 6 underwent thermal decomposition at 210 +/- 5 deg C to form naphthalene and benzobarrelene.
- Lin, Cheng-Tung,Wang, Nae-Jen,Yeh, Yu-Lin,Chou, Teh-Chang
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p. 2907 - 2928
(2007/10/02)
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