The reaction of 2-alkylcycloalkanones with iodine–cerium(IV) salts in alcohols (methanol, ethanol, propan-1-ol or propan-2-ol) gave the respective oxo ester in 28–98% yields.
References
1.
ItoS., and MatsumotoM., J. Org. Chem., 1983, 48, 1133.
KanedaK., KiiN., JitsukawaK., and TeranishiS., Tetrahedron Lett., 1981, 22, 2595.
5.
El AliB., BregeaultJ-M., MerrierJ., MartinJ., MartinC., and ConvertO. J., J. Chem. Soc., Chem. Commun., 1989, 825.
6.
AtlamsaniA., and BregeaultJ.-M., J. Org. Chem., 1993, 58, 5663.
7.
(a) HoriuchiC. A., SuzukiY., TakahashiM., and SatohJ. Y., Chem. Lett., 1987, 393; (b) C. A. Horiuchi and Y. Suzuki, Bull. Chem. Soc. Jpn., 1989, 62, 2919; (c) C. A. Horiuchi, H. Kiyomiya, M. Takahashi and Y. Suzuki, Synthesis, 1989, 785.
8.
(a) HoriuchiC. A., and KijiS., Chem. Lett., 1988, 31; (b) C. A. Horiuchi, Y. Nishio, D. Gong, T. Fujisaki and S. Kiji, Chem. Lett., 1991, 607; (c) C. A. Horiuchi, K. Ochiai and H. Fukunishi, Chem. Lett., 1994, 185; (d) C. A. Horiuchi, H. Fukunishi, M. Kajita, A. Yamaguchi, H. Kiyomiya and S. Kiji, Chem. Lett., 1991, 1921; (e) C. A. Horiuchi and E. Takahashi, Bull. Chem. Soc. Jpn., 1994, 67, 271.
9.
HoriuchiC. A., and KijiS., Bull. Chem. Soc. Jpn., 1997, 70, 421.
10.
HoriuchiC. A., IkedaA., KanamoriM., HosokawaH., SugiyamaT., and TakahashiT., J. Chem. Res. (S), 1997, 60.
11.
(a) DaubW. G., ZuckermannR. N., and JohnsonW. S., J. Org. Chem., 1985, 50, 1599; (b) T. Ishida and K. Wado, J. Chem. Soc., Perkin Trans. 1, 1979, 323; (c) R. S. Randad, N. G. Bhat and G. H. Kulkarni, Indian J. Chem., Sect. B, 1984, 22, 947; (d) K. I. Kohdair, A. A. Magd, K-K. S. Hussain, H. M. Khairy and E-K. M. Ahmed, Rev. Roumaine Chim., 1983, 28, 921; (e) A. E. Berhanu and G. Sendaba, J. Chromatogr., 1985, 3, 440; (f) S. Takano, K. Masuda and K. Ogasawara, Heterocycles, 1981, 16, 1509; (g) B. M. Vivekananda, M. Ravindranathan, S. Viswanatha and R. G. Venkoba, J. Org. Chem., 1984, 49, 3170; (h) T. Mukaiyama, M. Araki and H. Takei, U.S. Nat. 3,867,453, (Cl. 260-570AB; C07c), 18 Feb. 1975.