Advanced organic synthesis: methods and techniques by Richard S. Monson

By Richard S. Monson

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HYDROBORATION transfer of the diborane. After cooling, the generator is disconnected from the hydroboration flask. The excess diborane in the hydroboration flask is decomposed by the cautious addition of 20 ml of water. the addition of 32 ml of 3 W sodium hydroxide, followed by dropwise addition of 32 ml of 30 % hydrogen peroxide FIG. 1. Apparatus for the external generation of diborane. to the stirred solution maintained at 30-50° (water bath). The reaction mixture is stirred for an additional hour, and 100 ml of ether is added.

77, 48 (1955). 4. A. C. Cope and E. Ciganek, Org. Syn. Collective Vol. 4, 339 (1963). 5. E. L. EHeI, Rec. Chem. Progr. 22, 129 (1961). 6. E. L. Eliel, R. J. L. Martin, and D. Nasipuri, Org. Syn. 47, 16 (1967). 7. R. A. Daignault and E. L. Eliel, Org. Syn. 47, 37 (1967). 8. Y. M. Y. Haddad, H. B. Henbest, J. Husbands, and T. R. B. Mitchell, Proc. Chem. Soc. London, p. 361 (1964). 9. E. L. Eliel, T. W. Doyle, R. O. Hutchins, and E. C. Gilbert, cited in M. Fieser and L. Fieser, "Reagents for Organic Synthesis," Vol.

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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