By Richard S. Monson

ISBN-10: 0125049501

ISBN-13: 9780125049504

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The product of the reduction has bp 94-96°/3 mm. IV. Reduction of a,^-Unsaturated Ketones in Hexamethylphosphoric Triamide Hexamethylphosphoric triamide (HMPT) is a high-boiling solvent particularly satisfactory for dissolving metals or organometallic compounds. -unsaturated ketones by alkali metals. 14 mole) and anhydrous ether (30 ml) are introduced. 25 g-atom) is then added V. REDUCTION OF A y-DIKETONE WITH ZINC 29 in one portion with stirring. After 5 minutes the solution becomes deep blue and the temperature rises.

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. ), Vol. 3, Academic Press, New York, 1964. 8. N. S. Isaacs, "Experiments in Physical Organic Chemistry," p. 276. Macmillan, London, 1969. 9. F. L. Greenwood and M. D. Kellert, /. Amer. Chem. Soc. 75, 4842 (1953); F.

M. Downie, J. B. Holmes, and J. B. Lee, Chem. 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.

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Advanced Organic Synthesis by Richard S. Monson


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