Collect. Czech. Chem. Commun. 1984, 49, 244-252

13C and 15N NMR spectra of 6-substituted bicyclo[3,3,1]7-nonanone nitronates

Vladimír Macháčeka and Antonín Lyčkab

a Institute of Chemical Technology, 532 10 Pardubice
b Research Institute of Organic Syntheses, 532 18 Pardubice - Rybitví


13C and 15N NMR spectra (at the natural abundance level of 15N) have been measured and interpreted for bicyclic reaction products from 1,3,5-trinitrobenzene and cyclohexanone (I), cycloheptanone (II), cyclooctanone (III), acetone (IV), 2,4-pentanedione (V), 3-methyl-2,4-pentanedione (VI), 1-phenyl-1,3-butanedione (VII), and methyl acetoacetate (VIII). The compounds I-IV and VI exist in keto form, the compounds V, VII, and VIII are mixtures of keto and enol forms. Slow keto-enol equilibria in hexadeuteriodimethyl sulphoxide solutions of VII and VIII have been followed by 13C NMR spectra.