2 PRODUCTS OF RING-OPENING REACTIONS OF AN ARYLTHIONITROOXIRANE

Crystal structure determination of the products, S-(4-methylphenyl) (alpha R,4R)-alpha-bromo-2,2-dimethyl-1,3-dioxolane-4-thioacetate, C14H17BrO3S, (2), and S-(4-methylphenyl) (alpha R,4R)-alpha-(benzyloxycarbonylamino)-2,2-dimethyl-1,3-dioxolane-4-thioacetate C22H25NO5S, (3), Of the two reactions, including absolute-structure assignment, shows that they proceed stereospecifically with inversion of configuration. Common groups of the two structures have essentially the same bond lengths and angles, but different conformations, arising from weak hydrogen bonding and van der Waals interactions.