ISSN:
0894-3230
Keywords:
Organic Chemistry
;
Physical Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
,
Physics
Notes:
Nine 5-pyridylmethylenehydantoins were prepared. Each of the 1-methyl-substitute compounds was obtained in two stereoisomeric forms. Only one form of each of the 3-methyl-substituted and N-unsubstituted compounds was obtained directly from synthesis but could be partially converted into the other stereoisomer photochemically. The Z/E configurations and the conformational relationship between the pyridine and hydantoin rings were studied by 1H and 13C NMR spectroscopy, including variable-temperature 1H NMR. The existence of N—H…N or C—H…N interactions and the possibility of tautomerism are suggested for some of the compounds. The Z-isomers of compounds with 2- or 3-pyridyl rings prefer an s-cis conformation whereas the E-isomers prefer an s-trans conformation.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/poc.610030902
