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By Richard S. Monson

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Chem. , p. 2532 (1961). 16. E. A. Fehnel, S. Goodyear, and J. Berkowitz, /. Amer. Chem. Soc. 73, 4978 (1951). 17. E. L. Bennett and C. Niemann, /. Amer. Chem. Soc. 74, 5076 (1952). 18. D. S. Noyce, B. N. Bastian, P. T. S. Lau, R. S. Monson, and B. Weinstein, /. Org. Chem. 34, 1247 (1969). 7 Miscellaneous Elimination, Substitution, and Addition Reactions The following experimental procedures do not fall into any convenient categories, but all require reagents and techniques of general interest in organic synthesis.

1 g of 5 % rhodium on alumina for 16-18 hours at 50 psi initial pressure in a Parr apparatus. The reduction stops after the absorption of 1 equivalent of hydrogen. The catalyst is removed by filtration through celite, and the aqueous solution is carefully acidified with concentrated hydrochloric acid at 0°. The crude product is collected by filtration, dried in air, and recrystallized from benzene to give 1,3-cyclohexanedione, mp 105-107°. B. 1 g of 5% rhodium on alumina is hydrogenated at 50 psi in a Parr apparatus.

Tamm, and P. E. Aldrich, /. Amer. Chem. Soc. 91, 7315 (1969). 9. W. Huckel and W. Kraus, Chem. Ber. 92, 1158 (1959). Hydroboration A remarkable variation of the hydride reduction is the addition to double bonds of diborane (B2H6) (7). Easily generated by the reaction of boron trifluoride etherate with sodium borohydride, the reagent may be used in the generating solution or may be distilled into a receiving flask containing an ether as solvent. Diborane reacts with unsaturated polar functional groups with results similar to those of the metal hydride reducing agents.

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