A13C NMR study of twenty-one 4.4dimethyl-2-phenyl-l.3-oxazolines has shown that the chemical shifts of the oxazoline moiety are insensitive towards substitution on the phenyl ring.
Carbon-13 NMR chemical shifts in some substituted 1,2,4-triazol-3-ones
✍ Scribed by William M. Litchman; Ulrich Hollstein; E. Paul Papadopoulos
- Publisher
- John Wiley and Sons
- Year
- 1978
- Tongue
- English
- Weight
- 643 KB
- Volume
- 11
- Category
- Article
- ISSN
- 0749-1581
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✦ Synopsis
Abstract
Carbon‐13 NMR data for 15 substituted 1,2,4‐triazol‐3‐ones are presented and discussed with regard to enolization in the neutral molecules. The coupling constant and chemical shift data show that the proton at N‐2 is not exchanging rapidly in the DMSO‐d~6~ solvent. Using D~2~OOD^−^ as a solvent, it is found that the C‐3 and C‐5 resonances are shifted downfield by nearly the same amount, suggesting that the proton at N‐4 is being removed. Enolization in the neutral molecules does not occur to any significant extent.
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Complete 13C NMR chemical shift assignments are reported for 32 cyclic and one acyclic 1.3-diketones, either unsubstituted or having one or two substituents at the 2-position. The first two classes exist exclusively in the enol form in (CD,),SO and as mixed tautomers in CDCI,.