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Lnd. (London), p. 900 (1966). J. B. Lee and I. M. Downie, Tetrahedron 23, 359 (1967). A. W. Friederang and D. S. Tarbell, /. Org. Chem. 33, 3797 (1968). G. A. Wiley, R. L. Hershkowitz, B. M. Rein, and B. C. Chung, /. Amer. Chem. Soc. 86,964 (1964). D. Levy and R. Stevenson, J. Org. Chem. 30, 3469 (1965). J. P. Schaefer, J. G. Higgins, and P. K. Shenov, Org. Syn. 48, 51 (1968). REFERENCES 53 7. C. Djerassi, Chem. Rev. 43, 271 (1948); L. Horner and E. H. Winkelmann in "Newer Methods of Preparative Organic Chemistry" ( W.

The fraction boiling at 64-65°/14 mm or 72-73°/22 mm is used in the reduction. 38 mole) is dissolved in 100 ml of anhydrous ether. 25 g) is added, and the mixture is hydrogenated in a Parr apparatus at an initial pressure of 50 psi. Initially the reaction mixture becomes warm. The absorption of 2 mole equivalents of hydrogen takes 4-6 hours. The mixture is filtered by suction to remove the catalyst, and the filtrate is distilled at atmospheric pressure through a short fractionating column. 40 5.

2b. P. von R. Schleyer, M. M. Donaldson, R. D. Nicholas, and C. Cupas, Org. Syn. 42, 8 (1962). 3. J. C. Sircar and A. I. Meyers, /. Org. Chem. 30, 3206 (1965). 4. D. S. Noyce, G. L. Woo, and B. R. Thomas, /. Org. Chem. 25, 260 (1960). 5. W. M. Pearlman, Org. Syn. 49, 75 (1969). 6. J. A. Osborn, F. H. Jardine, J. F. Young, and G. Wilkinson, /. Chem. Soc. (A)1 p. 1711 (1966). 7. A. J. Birch and K. A. M. Walker, /. Chem. Soc. (C), p. 1894 (1966). 8. J. A. Osborn and G. Wilkinson, Inorg. Syn. 10, 67 (1967).

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