Alicyclic Chemistry: Volume 4: A Review of Chemical by Royal Society of Chemistry, W. Parker, Parker W

By Royal Society of Chemistry, W. Parker, Parker W

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2915; M. J. S. Dewar, S. Kirschner, and H. W. Kollmar, J. Arner. , 1974, 96, 5240; D. M. , p. 5959; H. Nohira, Tetrahedron Letters, 1974, 2573. M. Bigwood and S. S. Chem. , 1974, 529; H. Kessler, Tetrahedron, 1974,30, 1861. J. M. Photis and L. A. Paquette, J. Arner. Chem. ,1974, 96,4715. T. Tezuka, 0. Seshimoto, and T. S. Chem. , ,1974, 373. F. Mathey and J. P. Lampin, Fr. P. 2 171 596. ,197481,25805). D. 1. Schuster and C. W. Kim, J. Amer. Chem. , 1974,96, 7437. K. Shudo and T. Okamoto, Chem. and Pharm.

Oshima, Bull. Chern. Soc. 467. T. Negri, T. Kaneda, H. Mizuno, T. Toyoda, Y. Sakata, and S. Misumi, Bull. Japan, 1974,47, 2398. Z98Similarly, the product (260) of condensation of keteniminylidenetriphenylphosphorane(259) with ketones reacts with further (259), yielding the phosphoranes (261). These may be isolable and/or react with further ketone to give the hitherto unknown, deeply coloured bismethylenecyclobutanedione bis-imine derivatives (262)’” Thermal fragmentation of the diene (263) proceeds by two independent pathways3” leading to benzocyclobutene and 3-oxabicyclo[3,2,0]hepta-1,4-diene (264; X = 0).

Just and C. S. P. 3776940, 3776941 (Chem. , 1974, 80,95363,95364). Three- and Four-membered Rings 37 RRKM theory. -Breslow's group207has attempted to prepare 1,2,3-tribenzoylcyclopropene (148) by the route shown in Scheme 12. The desired product was evidently formed in the reaction mixture, but even when very hindered bases were used for the final dehydrohalogenation step the cyclopropene underwent further, complex changes and could not be isolated. :+A Ph CO , u+ H PhCO X = COPh PhCO--&-he,- PhCo X C1 or Br CO Ph x (147) PhOC COPh (148) Scheme 12 Another route examined was the addition of the ylide (147) to dibenzoylacetylene, followed by photochemical cyclization of the intermediate ylide (149).

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