Quantum chemical studies of the reaction of selenium dichloride with divinyl sulfide and comparison with experimental results

Quantum chemical studies of the reaction of selenium dichloride with divinyl sulfide have been carried out. The major reaction route (2,6-dichloro-1,4-thiaselenane → 5-chloro-2-chloromethyl-1,3-thiaselenolane → 2-chloromethyl-1,3-thiaselenole) and main trends of the reaction (a rearrangement of 2,6-dichloro-1,4-thiaselenane, facile selective dehydrochlorination of 5-chloro-2-chloromethyl-1,3-thiaselenolane), which have been determined by the quantum chemical studies, are in excellent agreement with experimental data.

Graphical abstractQuantum chemical studies of the reaction of selenium dichloride with divinyl sulfide have been carried out. The major reaction route (2,6-dichloro-1,4-thiaselenane → 5-chloro-2-chloromethyl-1,3-thiaselenolane → 2-chloromethyl-1,3-thiaselenole) and main trends of the reaction (a rearrangement of 2,6-dichloro-1,4-thiaselenane, facile selective dehydrochlorination of 5-chloro-2-chloromethyl-1,3-thiaselenolane), which have been determined by the quantum chemical studies, are in excellent agreement with experimental data.Figure optionsDownload full-size imageDownload as PowerPoint slide