Advanced organic synthesis: methods and techniques - download pdf or read online

By Richard S. Monson

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1,4-Naphthoquinone reacts in 30 minutes to give 1,2,3,4-tetrahydro-1,4-dioxonaphthalene in 70% yield. After recrystallization from hexane, the product has mp 95-97° (10). REFERENCES 1. F. J. McQuillin, in A. , "Technique of Organic Chemistry," Vol. II. Wiley/Interscience, New York, 1963. 2a. P. N. " Academic Press, New York, 1967. 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.

The preparation of one of the complexes is given, as well as some examples of its use. A. TRIS(TRIPHENYLPHOSPHINE)CHLORORHODIUM(I) (8) RhCl 3 + 4 P(C6H5)3 -> RhCl[P(C6H5)3]3 + C12P(C6H5)3 C12P(C6H5)3 + H2O -> OP(C6H5)3 + 2 HCl A 500-ml rcund-bottom flask is equipped with a reflux condenser, a gas inlet tube, and a gas outlet leading to a bubbler. The flask is charged with a solution of rhodium (III) chloride trihydrate (2 g) in 70 ml of 95 % ethanol. A solution of triphenylphosphine (12 g, freshly recrystallized from ethanol to remove the oxide) in 350 ml of hot ethanol is added to the flask, and the system is flushed with nitrogen.

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. L. Greenwood, M. D. Kellert, and J. Sedlak, Org. Syn. Collective Vol. 4, 108 (1963). 10. H. J. Dauben and L. L. McCoy, /. Amer. Chem. Soc. 81, 5405 (1959). 11. H. O. House and H. W. Thompson, /. Org. Chem. 28, 360 (1963). 12. H. O. House and R. W. Bashe, /. Org. Chem. 30, 2942 (1965). 13. A. Butenandt and A. WoIfT, Chem. Ber. 68B, 2091 (1935).

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Advanced organic synthesis: methods and techniques by Richard S. Monson

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