Quasi-concerted allylic rearrangement in the reaction of allylic chlorides with methyltin tris(methyl thiolate).

An attractive reaction mechanism, not yet established conclusively, involves the discharge of unsymmetrical (allylication)/MeSn (SMe)(n) Cl(4-n) ion pairs (n=1-3) via MeS ligand transfer. The implications of this investigation for the thermal stabilization of poly(vinyl chloride) are considered briefly, and the C- 13 NMR chemical shifts of several allylic chlorides and methyl sulfides are uses to derive parameters that can be employed for shift predictions.