Advanced Organic Synthesis, Methods and Techniques by Richard S. Monson

By Richard S. Monson

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Fieser and L. Fieser, "Reagents for Organic Synthesis," Vol. 2, p. 228. Wiley/Interscience, New York, 1969. 10. A. Zurqiyah and C. E. Castro, Org. Syn. 49, 98 (1969) and references cited therein. Dissolving Metal Reductions Although once used extensively for the reduction of functional groups, reactions employing dissolving metals have largely been replaced by other more convenient methods. Nevertheless, certain synthetic sequences that may require stereospecific or functionally selective reductions may best be executed by means of metals in solution.

6 ml) in diglyme (10 ml) is added from the dropping funnel over a period of about 15 minutes. The reaction mixture is now stirred for an additional 20 minutes, and water (10 ml) is carefully added to destroy the slight excess of borohydride. When no further hydrogen is evolved, the solution is made alkaline by the addition of 15 ml of dilute sodium hydroxide solution, followed by 15 ml of 30% hydrogen peroxide solution added in 2-3 ml portions. The reaction mixture is now poured into a separatory funnel with 50 ml of ice water, and the cyclohexanol is removed by two ether extractions.

Chem. 20, 1767 (1955). 7. P. Angibeaud, M. Larcheveque, H. Normant, and B. Tchoubar, Bull. Soc. Chim. , p. 595 (1968). 8. E. E. van Tamelen, M. Shamma, A. W. Burgstahler, J. Wolinsky, R. 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.

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