Syntheses and 13C nmr spectra of a number of cis and trans 2-(haloaryl)-2-[(1H-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 13C 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.

This study demonstrates the synthesis and 13C NMR spectra of cis and trans 2-(haloaryl)-2-[(1H-imidazol-1-yl)rnethyl]-4-(hydroxymethyl)-1,3-dioxolanes, with some

Paper

Synthesis and 13C NMR spectra of cis- and trans-{2-(haloaryl)-2-[(1H-imidazol)-1-yl]methyl]}-1,3-dioxolane-4-methanols

References

Citations