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Alicyclic chemistry. Vol. 6 : a review of the literature by M A McKervey, Chemical Society

By M A McKervey, Chemical Society

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Lev, J . Amer. Chem. ,1976,98,5697; (b) J. P. Catteau, P. Karafilogloy A. Lablache-Combier, N. Lethan, and G. Surpateanu, Tetrahedron, 1976,32,461; A. LablacheCombier and G. Surpateanu, Tetrahedron Letters, 1976, 3081. R. J. Norstrom, H . E. Gunning, and 0. P. Strausz, J . Amer. Chem. , 1976,98, 1454. Alicyclic Chemistry 24 exclusive cleavage of the bond between the methylene- and difluoro-substituted carbon atoms. However, with added tetramethylethylene, the difluoromethylenetetramethylcyclopropane (77) produced is stable.

Tatsano, and A. Konishi, Japan. Kokai 764150 (Chem. A h . 1976, 85, 32503). S. H. Goh, K. C. Chan, and H. L. Chong, Austral. J . , 1976,29, 1699. H. Prinzbach, V. Wessely, and H. Fritz,Tetrahedron Letters, 1976, 2765. G. Kaup and K. RBsch, Angew. Chem. Znternat. , 1976,15, 163; K. Menke and H. , p. 165; R. Nader and A. , p. 166. Thermal equilibration of (109) leads to (110) and the stable norcaradiene (1 11) which may also be a primary product of the cyclopropanation reaction. Although the details of the monocyclopropanation product of (106; R = C0,Me) are vague (a footnote in the communication), it would appear that the electron-withdrawing methoxy-carbonyl substituents make a significant contribution to the stability of the ‘norcaradieneophane’.

75 Br (59) (58) R=H 13% R = OBu' 30% (40; R = H) @ + 3rd 3r Br 60 40 Organometallic, Thermal, and Photochemical Methods. The Simmons-Smith cyclopropanation procedure has now been successfully applied to silyl vinyl ethers and 96 97 G. Klein and L. A. Paquette, Tetrahedron Letters, 1976, 2419. P. Hildenbrand, G. Schriider, and J. F. M. Oth, Tetrahedron Letters, 1976, 2001. (a) C . W. Jefford, V. de 10s Heros, and U. Burger, Tetrahedron Letters, 1976,703; (b)P. M. Kwantes and G. W. , p. 707. 99 Treatment of (60; R' = R2 = OSiMe,) under the usual condition results in the silyloxycyclopropane (61).

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