Synthesis of Vicinal Trioxo Compounds by Dimethyl Dioxirane Oxidation of 2-Diazo-1,3-dioxo Derivatives

References

• Murray , R. W. and Jeyaraman , R. 1985 . J. Org. Chem. , 50 : 2847
   Web of Science ®Google Scholar
• Cassidei , L. , Fiorentino , M. , Mello , R. , Sciacovelli , O. and Curci , R. 1987 . J. Org. Chem. , 52 : 699
   Web of Science ®Google Scholar
• Adam , W. , Chan , Y. Y. , Cremer , D. , Gauss , J. , Scheutzow , D. and Schindler , M. 1987 . J. Org. Chem. , 52 : 2800
   Web of Science ®Google Scholar
• Curci , R. 1990 . Advances in Oxygenated processes , Edited by: Baumstark , A. L. Vol. 2 , Greenwich, CT : JAI . Chapter I. For recent reviews, see:
   Google Scholar
• Adam , W. , Hadjiarapoglou , Curci , R. and Mello , R. 1993 . Organic peroxides , Edited by: Ando , W. 195 – 219 . New York : Wiley . Chapter 4
   Google Scholar
• Rubin , M. B. 1975 . Chem. Rev. , 75 : 177 For a review on vicinal tri- and polycarbonyl compounds, see:
   Web of Science ®Google Scholar
• Ihmels , H. , Maggini , M. , Prato , M. and Scorrano , G. 1992 . Tetrahedron Lett. , 32 : 6215 The oxidation of α-diazomethyl ketones to labile α-oxo-aldehydes by dimethyl dioxirane has been recently reported:
   Web of Science ®Google Scholar
• Regitz , M. and Maas , G. 1986 . Diazo Compounds , Toronto : Academic Press .
   Google Scholar
• Caneko , C. and Katagiri , S. Jpn. Kokai Tokkio Koho JP 01, 100, 147 [89, 100, 147] .
   Google Scholar
• 1989 . Chem. Abstr. , 111 : 154173f
   Google Scholar
• The unhydrated polioxo compounds were obtained by sublimation, crystallization or distillation of the hydrated form, according to literature.
   Google Scholar
• 2-Diazo-dimenthyl-(−)-malonate, yellow solid, m. p. 69–70°C; IR 2120 cm−1; [α]22 D −122° (c 3.1, CHCl3); 1H-NMR (CDCl3, 300 MHz): δ 4.81 (2H, dt, J = 11.1, 4.8 Hz); 2.12–2.06 (2H, m); 1.90 (2H, m); 1.71–1.67 (4H, m); 1.52–1.38 (4H, m); 1.15–0.96 (6H, m); 0.90 (12H, d, J = 6.6Hz); 0.78 (6H, d, J = 6.6 Hz). 13C-NMR (CDCl3, 75 MHz): 160.7, 75.7, 46.9, 41, 34.1, 31.3, 26.2, 23.4, 21.7, 20.7, 16.4.
   Google Scholar
• 2,2-Dihydroxy-dimenthyl-(−)-malonate, white solid, m.p. 115–116°C; [α]22 D-62′ (C 2.8, CHCl3); 1H-NMR (CDCl3, 300 MHz): δ 4.84 (2H, dt, J = 10.8, 4.2 Hz); 4.78 (2H, m); 2.03–1.82 (2H, m); 1.89 (2H, m); 1.72–1.68 (4H, m); 1.59–1.36 (4H, m); 1.18–0.93 (6H, m); 0.92 (6H, d, J = 3.8 Hz); 0.89 (6H, d, J = 3.8 Hz); 0.77 (6H, d, J = 3.8 Hz). 13C-NMR (CDCl3, 75 MHz): 168.2, 90.22, 77.9, 46.8, 40.4, 33.9, 31.3, 25.8, 23.2, 21.8, 20.6, 16.9. Anal. (Calc. for C23H40O6): C, 67.03 (66.89); H, 9.48 (9.77).
   Google Scholar
• Danheiser , R. L. , Miller , R. F. , Brisbois , R. G. and Park , S. Z. 1990 . J. Org. Chem. , 55 : 159
   Web of Science ®Google Scholar
• Gosh , S. and Datta , I. 1991 . Synth. Commun. , 21 : 191
   Web of Science ®Google Scholar
• Popic , V. V. , Korneev , S. M. , Nikolaev , V. A. and Korobitsyma , I. K. 1991 . Synthesis , : 195
   Web of Science ®Google Scholar
• Findlay , J. A. and Radics , L. 1980 . Can. J. Chem. , 58 : 579
   Web of Science ®Google Scholar
• Swindells , D. C. N. , White , P. S. and J. A. 1978 . Can. J. Chem. , 56 : 2491
   Web of Science ®Google Scholar
• Tanaka , H. , Kuroda , A. , Murusawa , H. , Hatanaka , H. , Kino , T. , Goto , T. , Hashimoto , M. and Taga , T. 1987 . J. Am. Chem. Soc. , 109 : 5031
   Web of Science ®Google Scholar