By Randolph P. Thummel
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Extra info for Advances in Theoretically Interesting Molecules: Volume 3
P. C. J. Chem. , Chem. Commun. 1993, 1471. ; Shah, R. ; Ravikumar, K. J. Chem. , Chem. Commun. 1993, 1006. Sastry, G. ; Jemmis, E. ; Shah, S. R. J. Chem. , Perkin Trans. 2 1993, 1867. Clar, E. Polycyclic Hydrocarbons; Academic Press, New York, 1964 and references therein. Hanson, J. ; Nordman, C. E. Acta Cryst. B. 1976, B32, 1147. ; Kasai, N. J. Am. Chem. Soc. 1988, 110, 3578. ; de Meiere, A. J. Chem. , Chem. Commun. ; Bitterwolf, T. ; Valle, G. J. Chem. , Perkins Trans. 2, 1991, 233. Barth, W.
73 A recent modification of the procedure using more appropriate leaving groups appears promising. The linear cyclobutabenzocyclopmpene (84, rocketene) was obtained in acceptable yield from the acyclic derivative 83. 2. Strained, Fused, and Short-Lived Cycloproparenes Once it was recognized that cycloproparenes were isoiable compounds, although highly strained, the synthesis of still more strained cycloproparenes, at the limits of isolability became an obvious synthetic challenge. These limits were tested by lmposing additional strain on the molecules via fusion of additional small rings, via annulation of the cycloproparenes with additional benzene rings, and via out-of-plane deformation of the molecules by bridging of the 2,5-positions of 1.
3. Rearrangements . . . . . . . . . . . . . . . 4. Reactions with Transition Metal Reagents . . . . . . . . 5. Reactions of Alkylidenecycloproparenes . . . . . . . . . Acknowledgments . . . . . . . . . . . . . . . . References . . . . . . . . . . . . . . . . . . Advances in Theoretically Interesting Molecules Volume 3, pages 37-107. Copyright 9 1995 by JAI Press Inc. All rights of reproduction in any form reserved.
Advances in Theoretically Interesting Molecules: Volume 3 by Randolph P. Thummel