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(Aminoethynyl) Metalations, 12. Reactions of Ynamines with Olefins of the (Methylene)malonic Acid Type
Himbert, Gerhard,Brunn, Wolfgang
, p. 642 - 653 (2007/10/02)
The (silylethynyl)- and (stannylethynyl)amines 1 react in the same way like other ynamines 7 (H, Me and CO2Me in the β-position) with the olefins 3 of the methylenemalonic acid type to give the 1,3-butadiene derivatives 6 and 8.These products arise from the spontaneous electrocyclic ring opening of primarily formed -cycloadducts.By heating, the derivatives 6a and 6c bearing an ester group in the 1-position and a trimethylsilyl group in the 3-position formally loose methyl trimethylsilyl ether and form the methylenecyclobutenones 9 and 11.
