By Richard S. Monson
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Soc. 86, 1761 (1964) and references cited therein. 5. E. E. van Tamelen and W. C. Proost, J. Amer. Chem. Soc. 76, 3632 (1954). 6. M. Yanagita, K. Yamakawa, A. Tahara, and H. Ogura, /. Org. 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).
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).
The cooled solution is * The rate of reaction is variable requiring from 1-4 days. Fresh catalyst is added whenever the rate of hydrogen uptake markedly decreases. Added catalyst must first be wet with solvent. The hydrogen must be well evacuated, for opening the mixture to the atmosphere without such evacuation will produce a mixture that may explode on contact with fresh catalyst. t A eutectic mixture of diphenyl and diphenyl ether, available from Dow Chemical Co. V. HOMOGENEOUS CATALYTIC HYDROGENATION 43 diluted with 100 ml of isooctane and extracted three times with 50-ml portions of water.
Advanced Organic Synthesis. Methods and techniques by Richard S. Monson