The Synthetic Applications of Carbonyl Ylides Stabilized(Isolable) Carbonyl Ylides °Push-Pu" Stabilization David M. Barnes Evans Group Seminars, March 16, 1993 Arduengo, A.J., Ill; Janulis, E P, Jr. J. Am. Chem. Soc. 1983 iIsomunchnons Hamaguchi, M; Ibata, T. Tetrahedron Lett. 1974, 4475-4476. Isomunchnons cycloadd to dipolarophiles mEws·Ydes A: Hornbuckle S F. Chem. Rev. C6H4NO2 M. P Acc. Chem. Res. 1986. 19. 348. M.P.chem.Rev.1986,86,919939. PhH. reflux Hamaguchi, M; Ibata, T. Chem. Lett. 1975, 499-502. 35B-01 Ylides12/17991207PM- + : The Synthetic Applications of Carbonyl Ylides David M. Barnes Evans Group Seminars, March 16, 1993 Reviews - Ylides Padwa, A.; Hornbuckle, S. F. Chem. Rev. 1991, 91, 263-309. Padwa, A.; Krumpe, K. E. Tetrahedron. 1992, 48, 5385-5483. Padwa, A. Acc. Chem. Res. 1991, 24, 22-28. Carbenes Doyle, M. P. Acc. Chem. Res. 1986, 19, 348-356. Doyle, M. P. Chem. Rev. 1986, 86, 919-939. "Push-Pull" Stabilization Stabilized (Isolable) Carbonyl Ylides Cu(acac)2 - + - + PhH, 80 °C Hamaguchi, M.; Ibata, T. Tetrahedron Lett. 1974, 4475-4476. X = H, Br, OMe - + Hamaguchi, M.; Ibata, T. Chem. Lett. 1975, 499-502. hν + - Arduengo, A. J., III; Janulis, E. P., Jr. J. Am. Chem. Soc. 1983, 105, 5929-5930 "Isomünchnons" Isomünchnons cycloadd to dipolarophiles PhH, reflux quantitative 87% R1 R2 O R1 O R2 A B A B R1 O R2 N N2 O O X O2N CH3 N O O CH3 O2N X N O O CH3 O2N X N O O CH3 N O2N CH3O2C CO2CH3 N O O CH3 Ph C6H4NO2 O O CH3 Ph C6H4NO2 CO2CH3 CO2CH3 NPh O O NPh O O H3C N N CH3 O CH3 CH3 CF3 F3C CF3 F3C N2 CF3 F3C CF3 F3C O NMe2 Me2N 35B-01 Ylides 12/17/99 12:07 PM