135354-98-2Relevant academic research and scientific papers
Syntheses of amidines from thioamides, mediated by the N-heterocyclic carbene indazol-3-ylidene
Scherbakow, Swetlana,Namyslo, Jan C.,Gjikaj, Mimoza,Schmidt, Andreas
experimental part, p. 1964 - 1968 (2010/01/19)
On decarboxylation, 1,2-dimethylindazolium-3-carboxylate forms the N-heterocyclic carbene 1,2-dimethylindazol-3-ylidene in situ, which proved to be a suitable reagent for amidinations of the mono-thiolactams of succinimide and phthalimide. Georg Thieme Ve
Reaction of arylimodimagnesium with aromatic bifunctional nitriles: Competition and/or cooperation of functional groups affected by electron-accepting ability and location
Okubo, Masao,Sakata, Masayo,Iwatsu, Yuko,Tsurusaki, Nobuyuki,Nakashima, Sawako,Iwamoto, Yoshihito,Nonaka, Harumi,Yamauchi, Akira,Matsuo, Koji
, p. 242 - 252 (2007/10/03)
The reactions of aryliminodimagnesium [ArN(MgBr)2, IDMg] with p′-substituted p-cyanobenzophenones, 1-cyano-9-fluorenone, o-, m- and p-dicyanobenzenes and o-, m- and p-nitrobenzonitriles were examined, and the relative yields of products were referred to the previous results of electron spin resonance studies. The products of condensation with carbonyl and nitro groups and of addition to cyano groups were formed. From the variations of the yields caused by the molar ratio of the magnesium reagent versus substrates and by the substituents of both reactants, the preferred groups were determined. The groups of p- and m-substrates are consistent with the position of highest density of free electrons in the anion radicals, whereas those of the o-substrates are inconsistent The consistency indicates competition of functional groups reflecting the relative ability of single electron acceptance from the reagent, whereas the inconsistency is ascribed to cooperation of neighbouring groups for σ-complexation with the Mg atom of the reagent. The categories of competition and cooperation are discussed in relation to fundamental features and general governing factors proposed for the IDMg reactions of monofunctional substrates.
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.
