Reactions of 1,6-dioxaspiro[3.3]heptan-2-one derivatives

Abstract

5,5-Diphenyl- and 5-(trans- and cis-)phenyl-1,6-dioxaspiro[3.3]heptan-2-one (1a—c) were heated with anilin to give 3-hydroxy-2,2-diphenyl- and 3-hydroxy-cis- and -trans-2-phenyl-oxetan-3-ylacetanilide (2a—c) respectively. Treatment of compound (1a) with sodium hydroxide in ethanol followed by neutralization with carbon dioxide afforded ethyl 3-hydroxy-2,2-diphenyloxetan-3-ylacetate (3). Neutralization with hydro chloric acid instead of carbon dioxide afforded the γ-lactone derivatives, 4-hydroxy-4-[hydroxy(diphenyl)methyl](4) and 4-hydroxy-4-hydroxymethyl-5,5-diphenyl-tetrahydrofuran-2-one (5). Refluxing compound (1a) with acid in methanol afforded 4-benzoyl-4-phenyl-(6) and 4-hydroxy-4-[methoxy(diphenyl)methyl]-tetrahydrofuran 2-one (7).

Heating compounds (1b and c) with acid in methanol afforded the corresponding 4-hydroxy-4-[methoxy (phenyl)methyl]tetrahydrofuran-2-ones (9) and (10).