Advanced Organic Synthesis by Richard S. Monson

By Richard S. Monson

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Reggel, R. A. Friedel, and I. Wender,/. Org. Chem. 22, 891 (1957); W. G. Dauben, E. C. Martin, and G. J. Fonken, J. Org. Chem. 23, 1205 (1958). 4. G. Stork and S. D. Darling, /. Amer. Chem. 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.

The system is not as sensitive to moisture as the phosphine-carbon tetrahalide system (see preceding section), but it suffers from the disadvantage that hydrohalic acids are produced as the reaction proceeds. Nevertheless, sensitive compounds can be successfully halogenated by the system, as exemplified by the preparation of cinnamyl bromide from the alcohol. An important feature of this reagent is its ability to convert phenols to the corresponding bromides under laboratory conditions. Examples of these conversions are given.

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). Nevertheless, the present reaction still plays a role in the degredation of naturally occurring nitrogen-containing compounds, and it is included here as an example of the techniques employed. 35 mole) and 45 ml of methanol is placed in a 500-ml Erlenmeyer flask, covered with a watch glass, and allowed to stand at room temperature.

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