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Recrystallization from benzene gives the pure product, mp 65-66°. -methoxyphenol (59% yield). III. Allylic and Benzylic Bromination with 7V-Bromosuccinimide As mentioned in an earlier section (cf. Chapter 1, Section III), allylic positions are subject to attack by free radicals resulting in the formation of stable allyl radicals. A^-Bromosuccinimide (NBS) in the presence of free-radical initiators liberates bromine radicals and initiates a chain reaction bromination sequence by the abstraction of allylic or benzylic hydrogens.

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once used extensively for the reduction of functional groups, reactions employing dissolving metals have largely been replaced by other more convenient methods.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. The Birch reduction, or its modifications (I)9 employs a solution of an alkali metal in liquid ammonia or an aliphatic amine and is still widely used in connection with the reduction of aromatic or conjugated systems.

Butenandt and A. WoIfT, Chem. Ber. 68B, 2091 (1935). 14. M. Yanagita and K. Yamakawa, /. Org. Chem. 21, 500 (1956). 15. G. F. H. Green and A. G. Long, /. Chem. , p. 2532 (1961). 16. E. A. Fehnel, S. Goodyear, and J. Berkowitz, /. Amer. Chem. Soc. 73, 4978 (1951). 17. E. L. Bennett and C. Niemann, /. Amer. Chem. Soc. 74, 5076 (1952). 18. D. S. Noyce, B. 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.

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