Isomeric Mixture Analysis of Some Ring-opening Reactions of Styrene Oxide

Abstract

Mixtures of ring-opened and other products of reactions of acetic or benzoic acids, or ethanol, or phenol with styrene oxide under various conditions can be qualitatively and quantitatively analyzed without isolation of the components by the use of n.m.r. This method, in the case of the ester products, avoids confusing the initial ring-opening result with the results observed after subsequent acyl migrations which readily occur in this type of system.

Selectivity of the reaction of free radicals with styrene

“…The NMR spectrum was identical with that reported previously. 13 2-[4-(Benzoyloxy)-l,4-diphenylbutoxy]-l,l,3,3-tetramethylisoindoline (22) and 2-[4-(Benzoyloxy)-l,3-diphenylbutoxy]-l,l,3,3-tetramethylisoindoline (23). The compounds 22 and 23 were only partially resolved under the conditions used for preparative HPLC.…”

Three Routes for the Synthesis of 6-Benzyl-1-ethoxymethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5-carbaldehyde

“…6-Benzyl-1-ethoxymethyl-5-hydroxymethyl-1H-pyrimidine-2,4-dione (13) was formed in 91% yield (Scheme 4). 6-Benzyl-1ethoxymethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-5carbonitrile (14) was formed in 21% yield while 11% of the dialkylated product (15) was formed (Scheme 4).…”