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Wege, Tetrahedron, 1974,30,3945. 5 kcal mol-'. Wynberg3' has reported three syntheses of spiro[3,3] hepta- 1,5-diene (294),which are summarized in Scheme 23. This chiral hydrocarbon has been resolved uia diastere324 325 D N. C. Yang, R. V. Carr, E. Li, J. K. McVey, and S. A. Rice, J. Amer. Chem. ,1974,96,2297. L. A. Hulshof and H. Wynberg, J. Amer. Chem. Soc.. 1974,96,2191.

Van Lanen, J . Org. , 1974,39, 3360. G. Kiehl. J. Streith, and G. Taurand, Tetrahedron, 1974. 30, 2851. 198The norbornadien-7-one ketal (141) is a convenient source of bis-methoxycarbene. 199 T. Sasaki, S. Eguchi, and M. Mizutani, Org. Prep. Prored. , 1974, 6, 57; P. CrabM, Ger. , 1974, 81, 25191); G. Manuel, G. Cauquy, and P. Mazerolles, Syn. React. Inorg. Metal-Org. , 1974,4, 143. '')' R. W. Hoffmann, W. Lilienblum, and B. Dittrich, Chem. , 1974, 107. 3395. 201 Halogenocarbenes formed in the thermal decomposition of polyhalogenomethanes at 500--650°C can be trapped by cyclopentene and cyclohexene.

Kopecky, W. -G. Heine, J . Org. , 1974, 39, 515. E. K. G. Schmidt, Chem. ,1974, 107, 2440. B. S. Green and M. Rejto, J . Org. , 1974, 39, 3284. 5 c0 C)oi Three- and Four-membered Rings 51 0 Me 0 + 0 hv, ph,c: Oi,M H2°;E,N e 0 Me 0 / n O M e Me0 Me0 ((209) CH 0 C \C H 0 0 a +;40 hv __+ \ \ - Pb(OAc), \ \ 0 Scheme 18 There have been relatively few previous reports of addition of acrylonitrile to heteroatomic systems. 270 2-Acyl-thio270 Y. Matsuura, Tetrahedron Letters. 1974. 51 3. ~~~ Cycloaddition of diphenylthiiren 1,l -dioxide to enamines affords breakdown products of the initially formed sulphone, arising from ring-opening and loss of sulphur dioxide.

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