Anhydrous ferric chloride dispersed on silica gel induced ring enlargement of tertiary cycloalkanols. II : a convenient homologation of cycloalkanones, preparation of spiro systems and propella -γ-lactones

作者: A. Fadel , J. Salaun

DOI: 10.1016/S0040-4020(01)96528-7

关键词:

摘要: Abstract The reagent obtained by mixing anhydrous FeCl3 and silica gel induced, in the lack of any solvent, dehydration tertiary cycloalkanols, specific C4→C5 C5 →C6 enlargement, formation spiro compounds propella-γ- lactones cleavage tetrahydropyranyl ethers.

参考文章(43)
Derek Redmore, C. David Gutsche, Carbocyclic ring expansion reactions ,(1968)
Tsutomu Fujita, Shoji Watanabe, Kyoichi Suga, Yoshiki Higuchi, Tsukasa Sotoguchi, A CONVENIENT PREPARATIVE METHOD OF (M.N.3)PROPELLA-Γ-LACTONES Journal of Organic Chemistry. ,vol. 49, pp. 1975- 1977 ,(1984) , 10.1021/JO00185A028
J.W.F.L. Seetz, F.A. Hartog, H.P. Böhm, C. Blomberg, O.S. Akkerman, F. Bickelhaupt, A direct synthesis of 1,3-bis(bromomagnesio)propane Tetrahedron Letters. ,vol. 23, pp. 1497- 1500 ,(1982) , 10.1016/S0040-4039(00)87142-7
Robert E. Ireland, William C. Dow, Jollie D. Godfrey, Suvit Thaisrivongs, Total synthesis of (±)-aphidicolin and (±)-β-chamigrene Journal of Organic Chemistry. ,vol. 49, pp. 1001- 1013 ,(1984) , 10.1021/JO00180A010
P. Canonne, G. Fytas, D. Thibeault, Annelation dans la serie des dialkyl-4,4 isoxazolones-5 Tetrahedron Letters. ,vol. 24, pp. 2991- 2994 ,(1983) , 10.1016/S0040-4039(00)88077-6
J.P. Barnier, J. Salaün, Spirovetivanes from silylated 1-hydroxycyclopropanecarboxaldehyde. Tetrahedron Letters. ,vol. 25, pp. 1273- 1276 ,(1984) , 10.1016/S0040-4039(01)80132-5
Vincent J. Traynelis, William L. Hergenrother, Harry T. Hanson, John A. Valicenti, Dehydration of Alcohols, Diols, and Related Compounds in Dimethyl Sulfoxide1 Journal of Organic Chemistry. ,vol. 29, pp. 123- 129 ,(1964) , 10.1021/JO01024A028
Jerry D. Buhler, Reaction of lithium alkyls with aldehydes and ketones. General study Journal of Organic Chemistry. ,vol. 38, pp. 904- 906 ,(1973) , 10.1021/JO00945A012