THEORETICAL-STUDIES ON THE CYCLIZATION PROCESS OF A NEW ORGANOSULFUR REACTION

The cyclization process of a new organosulfur reaction was studied by the MNDO (UHF) method. The first reaction path was assumed to be via t he organosulfur radical intermediate, the second via the ionic (cation ic and anionic) intermediates. The dehydroxylation process was assumed to occur with the synergistic cyclization. The results obtained indic ate that the potential energy barrier of the first reaction path was a bout 102 kcal mol(-1), and although the formation of the ionic interme diate is comparatively difficult, the potential energy barrier of the second path is comparable to the first. The sequential reaction path v ia the radical intermediate, i.e. first cyclization, then dehydroxylat ion, was investigated for comparison. The cyclization reaction was fou nd to be the thermodynamically favored process, while the ensuing dehy droxylation process was found to have a potential energy barrier of ab out 62 kcal mol(-1).