On the PPh3 catalyzed reaction between dibenzoylacetylene and vicinal -OH and -SH acids. One-pot synthesis of 1,3-dioxolane derivative

Abstract

AbstractThe efficient conjugate addition of vicinal - OH and - SH acids such as ethylene glycol and 1,2-ethanedithiol to dibenzoylacetylene in the presence of PPh3 leads to different products depending on the reaction conditions. Ab initio calculations at HF/6-31G* level shows that the unsymmetrical envelope conformation of 2,2-disubstituted 1,3-dioxolane 1 is more stable than the half-chair and Cs symmetric envelope forms.