Premium
Synthesis and 13 C NMR spectra of cis‐ and trans ‐{2‐(haloaryl)‐2‐[(1 H ‐imidazol)‐1‐yl]methyl]}‐1,3‐dioxolane‐4‐methanols
Author(s) -
Chapman David R.,
Bauer Ludwig
Publication year - 1990
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570270738
Subject(s) - chemistry , dioxolane , stereochemistry , ring (chemistry) , chemical shift , nmr spectra database , cis–trans isomerism , hydroxymethyl , carbon 13 nmr , benzoates , medicinal chemistry , spectral line , organic chemistry , physics , astronomy
Syntheses and 13 C nmr spectra of a number of cis and trans 2‐(haloaryl)‐2‐[(1 H ‐imidazol‐1‐yl)rnethyl]‐4‐(hydroxymethyl)‐1,3‐dioxolanes are described. The haloaryl groups are 2,4‐dichloro, 2,4‐difluoro‐, 4‐chloro‐and 4‐bromophenyl. In these series, some of the cis compounds become available through crystalline bromo benzoates 5 . Separations of some trans isomers are achieved through fractional crystallizations of imidazolyl benzoate nitrates 6 . Stereochemical assignments are based primarily on one major 13 C chemical shift difference, namely that of C‐4 of the 1,3‐dioxolane ring, the chemical shift of the trans isomers being 1.0‐2.5 ppm downfield from that of the cis isomers.