By M.F. Semmelhack
Quantity four specializes in additions and the ensuing substitutions at carbon-carbon &pgr;-bonds. half 1 comprises procedures in most cases regarded as uncomplicated polar reactions, reactive electrophiles and nucleophiles including to alkenes and alkynes. an incredible subject is Michael-type addition to electron poor &pgr;-bonds, featured within the first six chapters. partly 2 are accumulated the 4 normal approaches resulting in nucleophilic fragrant substitution, together with radical chain strategies and transition steel activation via to &pgr;-complexation. Metal-activated addition (generally via nucleophiles) to alkenes and polyenes is gifted partially three, together with allylic alkylation catalyzed via palladium. The assurance of nonpolar additions partly four contains radical additions, organometal addition (Heck reaction), carbene addition, and 1,3-dipolar cycloadditions.
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Additional resources for Additions to and Substitutions at C-C &pgr;-Bonds, Volume 4
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. 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.
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). C/s-J2-5,8-OCTALINDIONE (8) O Zn/HOAc 30 3. DISSOLVING METAL REDUCTIONS Six grams of the quinone-butadiene adduct are dissolved in 25 ml of 95% acetic acid and the solution is placed in a round-bottom flask fitted with a thermometer and a mechanical stirrer.
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. I. Methylenecyclohexane by Pyrolysis of an Amine Oxide The pyrolysis of amine oxides is a reliable synthesis of unrearranged olefins.
Additions to and Substitutions at C-C &pgr;-Bonds, Volume 4 by M.F. Semmelhack