(1R,5R)‐(+)‐Verbenone of High Optical Purity

作者: Mark R. Sivik , Kenetha J. Stanton , Leo A. Paquette

DOI: 10.1002/0471264180.OS072.08

关键词:

摘要: (1R,5R)-(+)-verbenone of high optical purity reactant: (1R)-(+)-α-Pinene (25.0 g, 0.183 mol intermediate: mixture acetates product: verbenone Keywords: hydrolysis, esters and lactones; oxidation, CHOH  CO; oxidation, miscellaneous; rearrangements; benzene; bis(2,2,2-trichloroethyl) azodicarboxylate, explosion hazard; diethyl hazard; dimethyl hazard; lead tetraacetate, cancer suspect agent; sodium dichromate dihydrate, highly toxic, agent

参考文章(7)
G�nther Ohloff, Wolfgang Giersch, Access to Optically Active Ipsdienol from Verbenone Helvetica Chimica Acta. ,vol. 60, pp. 1496- 1500 ,(1977) , 10.1002/HLCA.19770600506
Herbert C. Brown, Prabhakar K. Jadhav, Manoj C. Desai, A convenient procedure for upgrading commercial (+)- and (-)-.alpha.-pinene to material of high optical purity Journal of Organic Chemistry. ,vol. 14, pp. 4583- 4584 ,(1982) , 10.1021/JO00144A037
D. V. Banthorpe, D. Whittaker, The Preparation and Stereochemistry of Pinane Derivatives Chemical Reviews. ,vol. 66, pp. 643- 656 ,(1966) , 10.1021/CR60244A002
R. Criegee, Neuere Untersuchungen über Oxydationen mit Bleitetraacetat Angewandte Chemie. ,vol. 70, pp. 173- 179 ,(1958) , 10.1002/ANGE.19580700702
G. H. Whitham, 423. The reaction of α-pinene with lead tetra-acetate J. Chem. Soc.. ,vol. 0, pp. 2232- 2236 ,(1961) , 10.1039/JR9610002232
A. Blumann, O. Zeitschel, Ein Beitrag zur Autoxydation des Terpentinöls Berichte der deutschen chemischen Gesellschaft. ,vol. 46, pp. 1178- 1198 ,(1913) , 10.1002/CBER.191304601154