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Kiji, and J. Furukawa, Tetrahedron, 1974,30,405. 249 Evidence for the transient formation of adamantene in the d e h a l o g e n a t i ~ nof~ ~ ~ the dihalides (198; X = Br or I) and of homoadamantene in the Cope e l i r n i n a t i ~ n ~ ~ ' of the N-oxide [199: X = N(O)Me,] and the Hoffmann elimination2s2of the quaternary ammonium hydroxide (199; X = NMe,+OH-) has been adduced from the isolation of cyclobutane-type dimers of these highly strained olefins. ~ X X Thermally254 and photochemically25 5 induced cross-condensations of two dissimilar olefins have also been reported.
Chem. , 1974,%, 3705. J. J. Dannenberg, T. M. Prociv, and C. Hutt, J. Amer. , 1974,96,913. Three- and Four-membered Rings 47 A further, somewhat more efficient route to the propellane is the electrochemical reduction of the dibromide (195; X = Br) at relatively negative electrode potentials. 243 Cyclobutanes have been. synthesized in a routine manner by the p h o t o ~ h e m i c a l and , ~ ~ ~r n e t a l - c a t a l y ~ e ddimerizations ~~~ of olefins. These reactions 242 243 244 245 246 K. B.
J. Ranfaing, B. Calas, J. M. Fabre, and L. Giral, Tetrahedron Letters, 1974, 1439; see also M. Larcheveque. A. Debal, and T. Cuvigny, Bull. chim France, 1974,1710. G. Stork and J. F. Cohen, J. Amer. Chem. , 1974,%, 5270. 43 Three- and Four-membered Rings formed in preference to cyclopentanes. This has been adapted into a general synthesis of functionalized cyclobutanes, and is illustrated by the preparation of ( f)-grandis01 (Scheme 16). 226 Treatment of the tosylate (174) with methanolic potash gives either the cyclobutyl ether (175; X = OMe) or cyclohexenone (176), depending on the reaction times.