CHEMISTRY 534 CARBON-CARBON DOUBLE AND TRIPLE FALL 2013 BOND FORMATION

I. General A. Carey and Sundberg, Part B, Ch. pp 111-121; Ch. 6, pp 408-414 (5th Ed. Part B, Ch. 2, pp 157-176; Ch. 6, 596-601; Ch. 8, 761-767 (olefin metathesis section not in the 4th Ed.) B. Carruthers and Coldham, Ch. 2, pp 105-154

C. S. Kelly in Comprehensive Organic Synthesis, Vol. 1, Additions to C-X π Bonds, Part 1; S. Schreiber, Ed.; Pergamon Press, 1991; pp 729-817

D. Nicoloau and Sorensen: Chapter 24, Amphoteronolide and Amphotericin II. Carbonyl Olefinations A. Wittig and Related Reactions of Phosphorus 1. B. E. Maryanoff and D. B. Reitz, Chem. Rev. 1989, 89, 863 2. J. Clayden and S. Warren, Angew. Chem., Int. Ed. 1996, 35, 241 3. H. J. Bestmann, Top. Curr. Chem. 1983, 109, 85-163 4. H. J. Bestmann, in Carbon-Carbon Bond Formation; R. L. Augustine, Ed.; M. Dekker,

1979; Ch. 3 5. M. Schlosser, Topics in Stereochemistry 1970, 5, 1 6. A. Maercker, Org. React. 1965, 14, 270 7. W. S. Wadsworth, Org. React. 1977, 25, 73 8. I. Gosney, A. Rowley, in Organophosphorus Reagents in Organic Synthesis; J. I. G.

Cadogan, Ed.; Academic Press, 1979; pp 17-153 9. K. Becker, Tetrahedron 1980, 36, 1717 10. Y. Kulkarni, Aldrichim. Acta 1990, 23, 31 11. W. Stec, Accounts Chem. Res. 1983, 16, 411 12. A. W. Johnson, Ylides and Imines of Phosphorus; Wiley-Interscience, 1993 13. E. Vedejs and M. J. Peterson, Top. Stereochem. 1994, 21, 1 B. Other Elements 1. Silicon: D. J. Ager, Synthesis 1984, 384 D. J. Ager, Org. React. 1990, 38, 1 2. Titanium: M. T. Reetz, Titanium Reagents in Organic Synthesis; Springer Verlag; 1986 R. H. Grubbs, Pure Appl. Chem. 1983, 55, 1733 H. Nozaki, Bull. Chem. Soc. Jpn. 1980, 53, 1698 S. H. Pine, Org. React. 1993, 43, Chapter 2 J. E. McMurry, Chem. Rev. 1989, 89, 1513 D. Lenoir, Synthesis 1989, 883 III. Eliminations A. Pyrolytic Reactions

1. Reviews: A. Krebs and J. Swienty-Busch in Comprehensive Organic Synthesis, Vol 6, Heteroatom Manipulation; E. Winterfeldt, Ed.; Pergamon Press, 1991; pp 949-973.

P. C. Astles, S. V. Mortlock and E. J. Thomas in Comprehensive Organic Synthesis, Vol. 6, Heteratom Manipulation, E. Winterfeldt, Ed.; Pergamon Press, 1991; pp 1011-1039

2. Acetates: C. H. DePuy, Chem. Rev. 1960, 60, 431 3. Amines: A. C. Cope, Org. React. 1960, 4, 317 4. Xanthates: H. R. Nace, Org. React. 1962, 12, 57 5. Sulfoxides: B. M. Trost, J. Am. Chem. Soc. 1976, 98, 4887 6. Selenoxides: K. C. Nicolaou, Selenium in Natural Products Synthesis; CIS Inc., 1984; pp

66-166 H. J. Reich, in Oxidation in Organic Chemistry; W. S. Trahanovsky, Ed.;

Academic Press, 1978; Vol. 5-C, pp 15-102 C. Paulmier, Selenium Reagent and Intermediates in Organic Synthesis;

Pergamon Press, 1986 H. Reich and S. Wollowitz, Org. React. 1993, 44, 1

B. Reductive Elimination 1. Review: P. Kocienski in Comprehensive Organic Synthesis, Vol. 6. Heteratom

Manipulation; E. Winterfeldt, Ed.; Pergamon Press, 1991; pp 975-1010 2. L. A. Paquette, Org. React. 1979, 25, 1 3. E. J. Corey, J. Am. Chem. Soc. 1965, 87, 934 4. G. H. Whitman, J. Chem. Soc., Perkin Trans. 1 1974, 433 5. J. D. White, J. Am. Chem. Soc. 1977, 99, 1172 6. D. H. R. Barton, J. Chem. Soc., Perkin Trans. 1 1974, 1794 IV. Fragmentations A. Heterolytic: C. A. Grob, in The Chemistry of Double Bonded Functional Groups; S.

Patai, Ed.; Wiley, 1977; Vol. 2, p 653 P. Weyerstahl and H. Marschall in Comprehensive Organic Synthesis, Vol.

6, Heteroatom Manipulation; E. Winterfeldt, Ed.; Pergamon Press; 1991; pp 1041-1070

B. Bamford-Stevens: R. H. Shapiro, Org. React. 1976, 23, 405 A. R. Chamberlin and S. H. Bloom, Org. React. 1990, 39, 1 C. Eschenmoser-Tanabe: A. Eschenmoser, Helv. Chim. Acta 1971, 54, 2986 D. Anionic: J. A. Marshall, Synthesis, 1971, 229 V. Alkene Metathesis A. A. Fürstner, Ed., Topics in Organometallic Chemistry, Vol. 1; Alkene Metathesis in Organic

Synthesis; Springer Verlag, 1998 B. A. Fürstner, Angew. Chem. Int. Ed. 2000, 39, 3012 C. R. H. Grubbs and S. Chang, Tetrahedron 1998, 54, 4413 D. M. Schuster and S. Blechert, Angew. Chem. Int. Ed. 1997, 36, 2036 E. A. Hoveyda and R. R. Schrock, Chem. Eur. J. 2001, 7, 945 F. R. H. Grubbs, S. J. Miller and G. C. Fu, Acc. Chem. Res. 1995, 28, 446 G. R. H. Grubbs, Ed.; Handbook of Metathesis, Vols. 1-3, Wiley-VCH, 2003 H. K. C. Nicolaou, P. G. Bulger, D. Sarlah, Angew. Chem. Int. Ed. 2005, 44, 4490 VI. Acetylenes and Allenes A. P. Stang and F. Diederich, "Modern Acetylene Chemistry" VCH, 1995; B. P. Stang and F. Diederich, R. R. Tykwinski, Eds. Acetylene Chemistry: Chemistry, Biology,

and Material Science, Wiley-VCH, 2005 B. L. Brandsma, "Preparative Acetylenic Chemistry", Elsevier, 1971 C. L. Brandsma, "Synthesis of Acetylenes, Allenes, and Cumulenes", Elsevier, 1981 D. S. Patai, Ed. "The Chemistry of Triple-Bonded Functional Groups", Wiley-Interscience,

1983, 2 Vols. E. H. F. Schuster and G. M. Coppola, "Allenes in Organic Synthesis", Wiley, 1984 F. S. Patai, Ed. "The Chemistry of Ketenes, Allenes, and Related Compounds", 1980 G. H. G. Viehe, "Chemistry of Acetylenes", Dekker, 1969 H. T. F. Rutledge, "Acetylenes and Allenes", Reinhold, 1969