Alicyclic Chemistry. Vol. 5 by W Parker;

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By W Parker;

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Garratt, J . Org. , 1975,40,2212. lo9 D. Bosse and A. de Meijere, Tetrahedron Letters, 1975,871. 3-foldexcess of reagent Scheme 13 The treatment of the cyclic vinyl ether (92) with di-iodomethane-zinc/copper couple does not lead to the corresponding oxabicycloheptane (93; X = H) since both the olefin and product cyclopropane are acid-sensitive. ' l o Other more routine Simmons-Smith applications have appeared. ' l 2 The generation of carbenoid (95) from bromoform by treatment with diethylzinc has resulted in a new and highly efficient ' 'lo '12 B A.

Chem. , 1975,97, 5434. J. C. Orr and J. Broughton, J . , 1975,40, 1949. G. Hogeveen, J . Amer. Chem. ,1975,97,1479. '^^ Quadricyclanes (171) afford (172) and (173) in a 1:1 ratio with arylsulphenyl chlorides. '^^ HOCO HOCO The cyclovitamin (1 76) undergoes acid-catalysed solvolysis to give vitamins (178a) and (179a) in a ratio of 13: 1. The marked stereoselectivity is ascribed to the intervention of cyclopropylcarbinyl cation (177) (having bisected geometry with respect to the cyclopropane ring; see Scheme 24), which does not favour collapse to (179).

1975,14, 32. l Z 5 J. Casanova and B. Waegell, Bull. Soc. chim. France, 1975,922. lZ6 E. F. Rothgery, R. J. Holt, and H. A. McGee, J . Amer. Chem. ,1975,97,4971. lZ7 H. Bakker, H. Steinberg, and Th. J. deBoer, Rec. Trau. , 1975,94,50. J. M. Figuera, J. Perez, and A. P. S. Faraday I , 1975,71, 1905. 12' W. Ando, T. Hagiwara, and T. Migiti, Bull. Chem. Japan, 1975,48,1951. 130 D. S. Wulfman, B. Poling, and R. S. McDaniel, Tetrahedron Letters, 1975,4519. lZ2 lZ4 28 Alicyclic Chemistry f a ~ h i 0 n .

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