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By M A McKervey, Chemical Society

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Extra info for Alicyclic chemistry. Vol. 6 : a review of the literature published during 1976

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Amer. Chem. ,1976,98,2668. I. 0. Shapiro, T. V. Leonova, Yu. I. Ranneva, Yu. S. Snagovskii, A. I. Shatenshtein, and Yu. S. Shabarov, Doklady Akad. , 1976,228,1357 (Chem. , 1976,85,123068); T. V. Leonova, I. Shapiro, Yu. I. Ranneva, 0. A. Subbotin, R. V. Kudryavtsev, Yu. S. Shabarov, and A. I. Shatenshtein, Zhur. org. , 1976,12, 579 (Chem. , 1976,84, 179346). S. Singh and R. E. Robertson, Canad. J . , 1976,54, 1246. 49 Three-membered Rings sium t-butoxide. 208 Alkylation at the bridge positions of a bicyclobutane has been well documented.

The presence of a 1-methoxy substituent on the naphthalene ring directs the addition of dichlorocarbene to the 3,4-bond, whereas 2-methoxynaphthalene undergoes 1,2-addition to give (53; R = OMe). ~~" 2-Methylnaphthalene also undergoes 1,2-~yclopropanation but the adduct (53; R = Me) is again unstable. '" 92 93 94 95 T. Sasaki, S. Eguchi, E. Ohno, and F. Nakata, J . Org. , 1976,41,2408. S . R. Landor, V. Rogezs. and H. R. S. Perkin I , 1976,2103. A. Doutheau and J. Gore, Bull. chim. France, 1976, 1189.

A) P. S. Skell, J. C. Day, and K. J. Shea, J . Amer. Chem. , 1976, 98, 1195; ( b ) J. B. Lambert and K. Kobayashi, J . Org. , 1976,41,671. P. G. Gassman, G. M. Lein, and R. Yamaguchi, Tetrahedron Letters, 1976, 3113. C. Descoins and D. Semain, Tetrahedron Letters, 1976, 745. ’ 86 The tricyclic ketone (170) undergoes cleavage of the peripheral cyclopropane ring bond on treatment with lithium in liquid ammonia as is expected from stereoelectronic control in dissolving-metal reduction of cyclopropyl ketones.

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