ISSN:
0749-1581
Keywords:
α-Cyclodextrin nitrate
;
β-Cyclodextrin nitrate
;
Hydroxylamine denitration
;
15N—O—C—1H shift correlations
;
Chemistry
;
Analytical Chemistry and Spectroscopy
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Hexakis(2,3,6-tri-O-nitro)-α-cyclodextrin and heptakis(2,3,6-tri-O-nitro)-β-cyclodextrin were prepared and the complete assignment of the 1H, 13C and 15N resonance signals in each case was achieved using homonuclear shift correlation experiments, one-bond 13C—1H and three-bond 15N—O—C—1H heteronuclear shift correlation measurements. The denitration of these cyclodextrin nitrates by hydroxylamine in pyridine was investigated to study its selectivity in preparing partially nitrated derivatives of these cyclodextrins. The sites of denitration were determined in each case using 13C and 15N NMR and the products were completely characterized. The results indicate that denitration of these cyclodextrin nitrates is a highly regiospecific reaction occurring at the 2-position only and giving rise to hexakis(3,6-di-O-nitro)-α-cyclodextrin and heptakis(3,6-di-O-nitro)-β-cyclodextrin, respectively.
Additional Material:
4 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/mrc.1260291008
