Carbanions lithies d'α'-cyanoéthers β,γ-insaturés—IV1: Réarrangements sigmatropiques [2.3] en série benzylique; préparation de cetones ortho-méthyl-arylées

作者: B. Cazes , S. Julia

DOI: 10.1016/0040-4020(79)87046-5

关键词:

摘要: Resume Cyanohydrins of aliphatic aldehydes are converted into ethers by benzylic bromides with phase transfer catalysis to give β-benzylic α'-cyanoethers. On treatment lithium di-isopropylamide, these compounds o-methylaryl ketones via a [2.3]-sigmatropic rearrangement the resulting carbanions and elimination cyanide.

参考文章(27)
J. Jenni, H. Kühne, B. Prijs, Über chelatbildende α‐aminocarbonsäure‐thioamide Helvetica Chimica Acta. ,vol. 45, pp. 1163- 1171 ,(1962) , 10.1002/HLCA.19620450414
John M. McIntosh, Phase-transfer catalyzed formation of cyanohydrin ethers and acetates Canadian Journal of Chemistry. ,vol. 55, pp. 4200- 4205 ,(1977) , 10.1139/V77-595
S. E. DINIZO, R. W. FREERKSEN, W. E. PABST, D. S. WATT, Synthesis of .alpha.-alkoxyacrylonitriles using substituted diethyl cyanomethylphosphonates Journal of Organic Chemistry. ,vol. 41, pp. 2846- 2849 ,(1976) , 10.1002/CHIN.197647191
Gilbert Stork, Luis Maldonado, Anions of protected cyanohydrins as acyl carbanion equivalents and their use in a new synthesis of ketones Journal of the American Chemical Society. ,vol. 93, pp. 5286- 5287 ,(1971) , 10.1021/JA00749A069
WILLIAM Q. BEARD, CHARLES R. HAUSER, Consecutive Ortho Substitution Rearrangements Starting with 2- and 4- Substituted Benzyltrimethylammonium Ions1 Journal of Organic Chemistry. ,vol. 25, pp. 334- 343 ,(1960) , 10.1021/JO01073A007
Bernard Cazes, Sylvestre Julia, New Synthesis of Elsholtzia Ketone Synthetic Communications. ,vol. 7, pp. 113- 117 ,(1977) , 10.1080/00397917709410064
Homer. Adkins, Richard M. Elofson, A. G. Rossow, Cowin C. Robinson, The Oxidation Potentials of Aldehydes and Ketones Journal of the American Chemical Society. ,vol. 71, pp. 3622- 3629 ,(1949) , 10.1021/JA01179A012
Donald J. Cram, Janet Allinger, Studies in Stereochemistry. XXVI. Solvolytic Rearrangements in the 1,2-Diphenyl-2-methyl-1-butanol System1 Journal of the American Chemical Society. ,vol. 79, pp. 2858- 2865 ,(1957) , 10.1021/JA01568A051