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27.6.1.6.2 Variation 2: By Reaction of 1,1-Dihalides with Potassium O-Ethyl Dithiocarbonate

DOI: 10.1055/sos-SD-027-00206

Dabdoub, M. J.Science of Synthesis, (200427234.

The treatment of tetrasubstituted geminal dibromides with 2 equivalents of potassium O-ethyl dithiocarbonate results in transient thioketones,[‌108‌,‌110‌] which are trapped in situ by the reaction with dienes, affording the corresponding DielsAlder adducts (Scheme 21). This reaction requires 2 equivalents of potassium O-ethyl dithiocarbonate because the mechanism is likely to involve substitution of a bromide by O-ethyl dithiocarbonate, followed by the elimination of the bromide and dithiocarbonate groups, promoted by a second equivalent of dithiocarbonate, to afford the desired thioketone.

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