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
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.