55019-54-0Relevant academic research and scientific papers
Methyl Shifts in 1,4-Dipoles from Sulfonyl Isocyanates and Ketene O,N-Acetals
Schaumann, Ernst,Marr, Torsten,Nimmesgern, Hildegard,Sieveking, Stefan
, p. 335 - 338 (2007/10/02)
At low temperature, sulfonyl isocyanates 1 react with ketene O,N-acetals 2 to give 1,4-dipoles 3.On warming, dipoles 3 rearrange in a formal O-->N methyl shift to give malonamides 4.A crossover experiment starting from 2a and 2b with a deuterated O-methyl group gave scrambling of the label and thus confirmed the intermolecular nature of the methyl transfer.
