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By James R. Hanson (ed.)

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Terpenoids and Steroids 48 2-exo-bromo-2-endo-nitrobornane (293) gives 15% of the cyclopentene (294) and ca. e. initial formation of campholenic nitrile (296) [the main product from pyrolysis at 300 “ Cin a sealed tube for 2 h of 2,2-dinitrobornane(297)],followed by bromination, would benefit from additional support. r. 228 (298) R = CD, (299) R = Me (300) (3011 (302) (303) If any one of the three ketones camphor (299), endo-isocamphanone (300), or exo-isocamphanone (301) is heated at high temperatures with potassium tbut oxide in t-butyl alcohol all three are obtained, because of homoenolization [via the enolate (302)l.

P. Lavergne, A. Leblanc, and Ph. Viallefont, Bull. Sci. nut. phys. Maroc, 1972, 52. 1 . Y . Gaoni, Tetrahedron, 1972, 28, 5525. C. Alexandre and F. Rouessac, Bull. Chem. Japan, 1972, 45, 2241. M . A. Cooper, C . M . Holden, P. Loftus, and D. S. Perkin If. 1973, 665. V. Hach, J . Org. , 1973, 38, 293. V. Hach and H . G . Higson, Canad. P. 914 214 (the formulae are incorrect in Chem. S. P. 708 521. -In this Report, after the chemistry of monoterpenoids with this ring system, a section concerning the various rearrangements between bicyclo[2,2,l]heptanes and bicyclo[3,l,l]heptanes is included.

155 IS6 15' R. M. Carman and B. N. Venzke, Austral. J . , 1973, 26, 571. G . Buchi and J. C. Vederas, J . Amer. Chem. ,1972, 94, 9128. A. J . Birch and K. P. Dastur, Austral. J . , 1973, 26, 1363. Terpenoids and Steroids 32 A n n. ’ 5 8 An examination of the reduction of carvone over palladium or platinum catalysts has once again shown how platinum catalysts are more selective than palladium catalysts, platinum black yielding only carvomenthone (184), carvotanacetone (185), and carvomenthol (186); far more intermediates are found using 10% palladium on charcoal, whereas with palladium black, isomerization to carvacrol (187) occurs.

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