By Richard S. Monson
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Extra resources for Advanced organic synthesis: methods and techniques
The product is isolated by distillation of the residue. Examples 1. 6 g of methyl isobutyl ketone, bp 117-118°/l atm and a residue of 3 g. 2. 3 mm, 207°/1 atm. 3. 1-Benzoylcyclohexene gives, after removal of the ether, phenyl cyclohexyl ketone, which is recrystallized from petroleum ether, mp 52° (80%). 4. J1(9)-Octalone-2-gives trans-2-decalone, bp 112-114°/13 mm. V. -unsaturated y-diketones can conveniently be done with zinc in acetic acid. The following procedure is applicable to the reduction of the Diels-Alder adduct of quinone and butadiene (Chapter 8, Section II).
Yanagita, K. 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.
R. Thomas, /. Org. Chem. 25, 260 (1960). 5. W. M. Pearlman, Org. Syn. 49, 75 (1969). 6. J. A. Osborn, F. H. Jardine, J. F. Young, and G. Wilkinson, /. Chem. Soc. (A)1 p. 1711 (1966). 7. A. J. Birch and K. A. M. Walker, /. Chem. 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.
Advanced organic synthesis: methods and techniques by Richard S. Monson