Mechanism and regioselectivity of the cycloaddition of thiones derived from Meldrum's acid, malonates, or other dicarbonyls.
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.
Perreault
Stéphane
S
Département de Chimie, Université de Sherbrooke, 2500 Boul. Université, Sherbrooke, QC, Canada J1K 2R1.
Poirier
Maude
M
Léveillé
Pascal
P
René
Olivier
O
Joly
Pascal
P
Dory
Yves
Y
Spino
Claude
C