Advanced Organic Synthesis, Methods and Techniques by Richard S. Monson

By Richard S. Monson

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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.

276. Macmillan, London, 1969. 9. F. L. Greenwood and M. D. Kellert, /. Amer. Chem. Soc. 75, 4842 (1953); F. L. Greenwood, M. D. Kellert, and J. Sedlak, Org. Syn. Collective Vol. 4, 108 (1963). 10. H. J. Dauben and L. L. McCoy, /. Amer. Chem. Soc. 81, 5405 (1959). 11. H. O. House and H. W. Thompson, /. Org. Chem. 28, 360 (1963). 12. H. O. House and R. W. Bashe, /. Org. Chem. 30, 2942 (1965). 13. A. Butenandt and A. WoIfT, Chem. Ber. 68B, 2091 (1935). 14. M. Yanagita and K. Yamakawa, /. Org. Chem.

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. The sequence showing the reduction of benzene to 1,4-cyclohexadiene is typical of the one-electron transfer mechanism commonly understood to pertain in such reductions.

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