Advanced Organic Synthesis by Richard S. Monson

By Richard S. Monson

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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. I. Methylenecyclohexane by Pyrolysis of an Amine Oxide The pyrolysis of amine oxides is a reliable synthesis of unrearranged olefins. Its importance in this regard, however, has largely been reduced by the development of the Wittig reaction (Chapter 11).

10 mm) is applied with stirring. Resolidification of the amine oxide indicates loss of the water of hydration. Thereupon, the bath temperature is raised to 160° and decomposition of the amine oxide occurs over about 2 hours. The distillate is mixed with water (100 ml) and the olefin layer is separated. The organic phase is washed twice with 5-ml portions of water, twice with 5-ml portions of ice-cold 10 % hydrochloric acid, and once with 5 ml of bicarbonate solution.

The mixture is extracted five times with 30-ml portions of ether, the combined ethereal extracts are washed with water and saturated salt solution, then dried, and the ether is evaporated. 4824. B. trans- 10-METHYL-2-DECALONE (6) CH 3 H The procedure given in the preceding experiment can be applied to the reduction of 10-methyl-J1(9)-octalone-2 prepared in Chapter 10, Section VI. 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.

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