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By Richard S. Monson

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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. 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).

React. 13, 1 (1963). H. C. Brown and G. Zweifel, /. Amer. Chem. Soc. 83, 1241 (1961). R. A. Benkeser and E. M. Kaiser, J. Org. Chem. 29, 955 (1964). Catalytic Hydrogenation The technique of catalytic hydrogenation can be applied almost universally to unsaturated systems, and therein lies its chief advantage (7). By appropriate selection of catalyst, pressure, and temperature, a remarkable variety of substrates can be made to undergo hydrogenation, many of them under hydrogen pressure not exceeding 50 psi (see Appendix 3 for description and use of low-pressure hydrogenation apparatus).

The melting point varies with the purity of the starting diene but is usually above 65°. II. , 100 atm) and high temperatures. However, the development of rhodium catalysts has alleviated these difficulties, allowing the low-pressure (50 psi) hydrogenation of phenols without attendant hydrogenolysis. , hydrogen-oxygen or methanol-oxygen) is to be avoided. Mild evacuation of the reaction vessel containing the catalyst prior to the introduction of hydrogen, and the flushing and evacuation of the vessel several times with hydrogen at low pressure will serve to prevent any difficulties.

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