The Preparation of 1-Dimethylamino-1-ethylthioethylene (Ketene-N, S-acetal) and Its Reactions with Some Electrophilic Reagents

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Abstract
The preparation of 1-dimethylamino-1-ethylthioethylene (ketene-N, S-acetal) from N, N-dimethylamino-S-ethylthioacetamidium iodide and the reactions of the ketene-N, S-acetal with some electrophilic reagents were investigated. One equivalent of phenyl isocyanate and two equivalents of diphenylketene reacted with the ketene-N, S-acetal to produce substituted acrylanilide and 2, 3-dihydro-α-pyrone derivative, respectively. On the other hand, the reactions of the ketene-N, S-acetal with carbon disulfide in the presence of elemental sulfur and with electrophilic oleflns, such as acrylonitrile and methyl acrylate, gave 5-dimethylaminotrithione and substituted cyclobutenes, respectively, by eliminating ethyl mercaptan. Further, it was found that α, β-unsaturated carbonyl compounds, such as acrolein and methyl vinyl ketone, afforded bicyclic compounds, 2, 10-dioxabicyclo[4. 4. 0]decadiene-3, 8 derivatives.