Chemo- and regioselective oxidation of adamantyl derivatives by dioxiranes
作者： Lucia D'Accolti , Ping Kang , Saeed Khan , Ruggero Curci , Christopher S. Foote
DOI: 10.1016/S0040-4039(02)00876-6
关键词: Chemistry 、 Oxide 、 Dioxirane 、 Regioselectivity 、 Chemoselectivity 、 Yield (chemistry) 、 Trifluoromethyl 、 Organic chemistry
摘要: Abstract Methyl(trifluoromethyl) dioxirane ( 1 ) gives direct chemo- and regioselective oxidation of methyleneadamantane oxide 2 isopropylideneadamantane 3 in high yield under mild conditions. Secondary CH are not appreciably oxidized regioselectivities were observed for attack at tertiary CH.
elsevier.com
sci-hub.se 参考文章(19)
M.A.J. Rodgers, E.L. Powers, Oxygen and oxy-radicals in chemistry and biology Academic Press. ,(1981)
H.W. Geluk, J.L.M.A. Schlatmann, Hydride transfer reactions of the adamantyl cation—II : Synthesis of 1,3- and 1,4-disubstituted adamantanes Tetrahedron. ,vol. 24, pp. 5369- 5377 ,(1968) , 10.1016/S0040-4020(01)96330-6
Thomas H. W. Poon, Kenneth Pringle, Christopher S. Foote, Reaction of Cyclooctenes with Singlet Oxygen. Trapping of a Perepoxide Intermediate Journal of the American Chemical Society. ,vol. 117, pp. 7611- 7618 ,(1995) , 10.1021/JA00134A005
Luigi Lopez, Piero Mastrorilli, Giuseppe Mele, Cosimo F. Nobile, Aerobic epoxidation of hindered olefins and enol ethers catalyzed by a polymerizable β-ketoesterate complex of iron(III) Tetrahedron Letters. ,vol. 35, pp. 3633- 3636 ,(1994) , 10.1016/S0040-4039(00)73259-X
Ashis Mukherjee, Qianhong Wu, William J. le Noble, Face selection in Claisen rearrangements Journal of Organic Chemistry. ,vol. 59, pp. 3270- 3274 ,(1994) , 10.1021/JO00091A010
Ruggero Curci, Lucia D'Accolti, Caterina Fusco, On the hydroxylation of bicyclo[2.1.0]pentane using dioxiranes Tetrahedron Letters. ,vol. 42, pp. 7087- 7090 ,(2001) , 10.1016/S0040-4039(01)01434-4
Robert D. Bach, Jose L. Andres, Ming Der Su, Joseph J. W. McDouall, Theoretical model for electrophilic oxygen atom insertion into hydrocarbons Journal of the American Chemical Society. ,vol. 115, pp. 5768- 5775 ,(1993) , 10.1021/JA00066A049
Rossella Mello, Michele Fiorentino, Caterina Fusco, Ruggero Curci, Oxidations by methyl(trifluoromethyl)dioxirane. II: Oxyfunctionalization of saturated hydrocarbons Journal of the American Chemical Society. ,vol. 111, pp. 6749- 6757 ,(1989) , 10.1021/JA00199A039
C Scholtissek, G Quack, H.D Klenk, R.G Webster, How to overcome resistance of influenza A viruses against adamantane derivatives Antiviral Research. ,vol. 37, pp. 83- 95 ,(1998) , 10.1016/S0166-3542(97)00061-2
Michael M. Bobek, Udo H. Brinker, Intra- and Intermolecular Diastereoselectivity of 5-Hydroxy-2-adamantylidene† Journal of the American Chemical Society. ,vol. 122, pp. 7430- 7431 ,(2000) , 10.1021/JA001123M