G. Borodkin, I. R. Elanov, M. M. Shakirov
Aug 1, 2003
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Journal
Russian Journal of Organic Chemistry
Abstract
It was established by means of multinuclear magnetic resonance method (1H, 13C, 19F and 14N) that reaction of 2,2,6,6-tetramethyl-4-R-piperidin-1-oxyl radicals (R = H, OH, OMe, OCOPh, NHCOMe) with nitrosonium tetrafluoroborate gave rise to the corresponding 2,2,6,6-tetramethyl-1-oxo-4-R-piperidinium tetrafluoroborates. Linear correlations were found between the chemical shifts of atoms H4, C4 of cations and respectively σ1-constants of substituents R and chemical shifts of C4 atom calculated from increments of substitution. The conformational features of the generated nitrosonium cations are considered on the grounds of vicinal coupling constants JHH and quantum-chemical calculations by AM1 method.