By Richard S. Monson
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Extra resources for Advanced Organic Synthesis: Methods and Techniques
Soc. (C), p. 1894 (1966). 8. J. A. Osborn and G. Wilkinson, Inorg. Syn. 10, 67 (1967). 9. C. Djerassi and J. Gutzwiller, /. Amer. Chem. Soc. 88, 4537 (1966). 10. A. J. Birch and K. A. M. , p. 3457 (1967). The Introduction of Halogen The introduction of halogen into organic molecules can be carried out by a variety of addition or substitution reactions. The classical methods for the addition of halogen to double bonds or the substitution of halogen for hydroxyl by hydrohalic acids are too well known to bear repetition here.
The ether layer is separated and the aqueous layer extracted with three 20-ml portions of ether. The combined ethereal extracts are washed with saturated sodium bicarbonate solution followed by saturated sodium chloride solution. The ethereal solution is dried over anhydrous potassium carbonate (20-24 hours), filtered, and concentrated by distillation at atmospheric pressure. 4610, in about 85% yield. III. Reduction with Iridium-Containing Catalysts A recently discovered reduction procedure provides a convenient route to axial alcohols in cyclohexyl derivatives (8).
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.