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By Richard S. Monson

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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). Easily generated by the reaction of boron trifluoride etherate with sodium borohydride, the reagent may be used in the generating solution or may be distilled into a receiving flask containing an ether as solvent.

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.

Triphenylphosphine is dried by dissolving it in dry benzene, removing the solvent under vacuum, and storing over phosphorus pentoxide. Alcohols should also be dried before use. 1 mole), 46 6. 11 mole), and 200 ml of anhydrous carbon tetrachloride. The flask is fitted with a condenser (drying tube) and refluxed (steam bath) for 2-3 hours. The flask is then cooled to room temperature and 200 ml of pentane is added to precipitate the bulk of the triphenylphosphine oxide. The mixture is filtered and the filtrate is fractionally distilled affording the product.

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