Alicyclic Chemistry. Vol. 5 by W Parker;

By W Parker;

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Itoh, N. Sasaki, and A. Suzuki, Synthesis, 1975, 317. L. Bagnall, A. Meisters, and T. Mole, Austral. J . , 1975,28, 821. S. Danishefsky and J. Dynak, Tetrahedron Letters, 1975, 79. R. L. Augustine and F. G. Pinto, J . Org. , 1975, 40, 115: J. G . Cannon and J. E. , p. 182. 233 Treatment of 1,l-dibromo-2-ethoxycyclopropane with alkoxide affords both alkyne and ring-opened acetal The availability of the cis- and trans-1 -lithio-2-methoxycyclopropanes(216) provides a new and useful method for chain lengthening by three carbon atoms, as illustrated in Scheme 33.

D. Graham, and U. , p. 4717. S . E. Kondrat'eva and S. I. Burmistrov, Zhur. orq. , 1975, 11, 197 [ J . Orq. Chem. ),1975, 11, 1911; V. F. Mironov, V. D. Sheludyakov, V. V. Shcherbmin. N. A. Viktorov, and 0. M. Rad'kova, Zhur. obshchei. , 1974,44, 2434 (Chem. , 1975,82, 125435), F. Anderson, J. M. Birchall, R. N. Haszeldine, and B. J. S. Perkin I I , 1975, 1051; H. M. Frey, G. E. Jackson, R. A. Smith, and R. S. Fataday I , 1975,71, 1991. J. L. Hahnfeld and D. J. Burton, Tetrahedron Letters, 1975, 1819.

Papadakis, Tetrahedron, 1975,31,165. J. Casanova and B. Waegell, Bull. chim. France, 1975,598. T. C. Clarke, L. A. Wendling, and R. G. Bergman, J . Amer. Chem. , 1975,97, 5638. 5% retention of optical purity, and predominantly doubly inverted) and (123) in nearly racemic form. 6% optical purity, and predominantly double retention of configuration). With the singly deuteriated analogues, (121) exhibits a deuterium isotope effect of about 10% on the optical purity of the products, while a real, but somewhat smaller, effect is observed with (122).

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