Stereochemical aspects of nucleophilic substitution at unsaturated fluorocarbon

Addition-substitution reactions of 2-thio-3-chloroacrylamides with carbon, nitrogen, oxygen, sulfur and selenium nucleophiles

“…[9][10][11][12] However, partial or complete stereoconvergence is also possible, 13,14 particularly when the carbanionic carbon bears two strongly electron withdrawing groups. The retention or loss of stereochemistry may be rationalised by relating the ability of the C 2 -C 3 single bond to rotate to the stability of the carbanion.…”