Christian Kaepplinger, R. Beckert, G. Braunerová, L. Zahajská, Anja Darsen, H. Goerls
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Barton–Kellogg olefination of conjugated dithioxo compounds
The first Barton–Kellogg olefination employing thioamides or thioureas as substrates is reported. Starting from the conjugated dithioxo compounds 1 and diazocompounds 2 we substituted the C˭S groups by ester substructures mono- (type 3) and obtained the disubstituted products 4. Using the same procedure, the tricyclic thiourea 5 was converted into a new ketene aminal 6. Intermediates such as primary cycloadducts or three-membered ring-contraction products could not be isolated for any reactions studied here.
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