84628-31-9Relevant academic research and scientific papers
Benzylic Azide Functionalization of Tautomeric o-Acyl-benzoic Acid, -benzamide, and -nicotinic Acid Derivatives, and Thermal Decomposition of the Derived Azides
Takeuchi, Hisato,Eguchi, Shoji
, p. 2149 - 2154 (2007/10/02)
A series of benzylic azido compounds were prepared by the reactions of o-acyl-benzoic acids and -benzamides and pyridine analogues with sodium azide, diphenylphosphoryl azide, and trimethylsilyl azide.Thermal decomposition of the derived benzylic azides afforded three types of rearrangement products.The selectivity of rearrangement depended on the migratory aptitude of substituents and on stereoelectronic factors.
NMR STUDIES ON IMIDINES. II. 1H AND 13C NUCLEAR MAGNETIC RESONANCE STUDY ON THE TAUTOMERISM AND GEOMETRICAL ISOMERISM OF 3-ARYLIMINOISOINDOLINONES.
Spiessens, Luc I.,Anteunis, J. O.
, p. 763 - 790 (2007/10/02)
3-Aryliminoisoindolinones 2 have been fully examined by 1H and 13C NMR spectroscopy.A complete analysis of 13C-1H coupling constant is given for three of the compounds (2c, 3a, 4b).Only the arrylimino tautomeric forms are presented in polar (DMSO-d6,; CD3OD) and apolar solvent (CDCl3) as established by comparaison of 1H and 13C NMR chemical shift values of 2 with those of suitable model compounds (3, 4, 6 and 7).It is shown that both the endo- and exocyclic N-methylated aryliminoisoindol(en)inones (3 and 4) adopt the E configuration (due to steric hidrance of the N-methyl group) but that the title compounds are present in solution as 4:1 mixtures of Z and E components (Figure 4).This is not the case for the 2'-pyridyl derivatives (2c, 2e, 2f) where the Z form benefits from an intramolecular hydrogen bond.An interesting proximity 13C chemical shift effect is produced by the variation in steric crowding in the E vs Z isomers of the title compounds.
