title: Mechanism and regioselectivity of the cycloaddition of thiones derived from Meldrum's acid, malonates, or other dicarbonyls.
abstract: Several alpha,alpha-dioxothiones were generated in situ and reacted with 1,3-dienes of varying electronic and steric properties. It was found that thiones 10a and 11a reacted well with electron-rich or electron-poor dienes and are complementary in their regioselectivities when steric effects are at play. The calculated preferred mechanistic pathway implies a thiiranium zwitterion intermediate.
authors.affiliation: Département de Chimie, Université de Sherbrooke, 2500 Boul. Université, Sherbrooke, QC, Canada J1K 2R1.
authors.forename: Stéphane
authors.initials: S
authors.lastname: Perreault
authors.forename: Maude
authors.initials: M
authors.lastname: Poirier
authors.forename: Pascal
authors.initials: P
authors.lastname: Léveillé
authors.forename: Olivier
authors.initials: O
authors.lastname: René
authors.forename: Pascal
authors.initials: P
authors.lastname: Joly
authors.forename: Yves
authors.initials: Y
authors.lastname: Dory
authors.forename: Claude
authors.initials: C
authors.lastname: Spino