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Paper | Regular issue | Vol 57, No. 2, 2002, pp.307-316
Published online, 1st January, 1970
DOI: 10.3987/COM-01-9407
Synthesis, 1H and 13C NMR Study of Pyrazoles Derived from Chiral Cyclohexanones (3-Methylcyclohexanone, Menthone, Pulegone, Dihydrocarvone and Carvone)

Robert Faure, Aline Frideling, Jean-Pierre Galy,* Ibon Alkorta, and José Elguero

*Laboratoire de Valoristation de la Chime Fine, Facluté des Sciences et Techniques de Saint Jérôme, Université d’Aix-Marseille III, Avenue Escardille Normandie Niemen (Case 552), 13397 Marseille Cedex 13, France

Abstract

The 1H and 13C chemical shifts of four tetrahydroindazoles (two of them existing as diastereomeric mixtures) and one aldazine were measured and assigned. These compounds were obtained from monoterpenic ketones (R)-(+)-3-methylcyclohexanone, (2S,5R)-(-)-menthone, (R)-(+)-pulegone, (5R)-(+)-dihydrocarvone, and (R)-(-)-carvone in a two-step procedure. The annular tautomerism in CDCl3 solution was calculated and compared with ab initio calculations (B3LYP/6-31G*).