54560-59-7Relevant articles and documents
The chemistry of the N-methyl-3-dehydropyridinium ylid
Pan, Weitao,Shevlin, Philip B.
, p. 5091 - 5094 (1997)
The reaction of atomic carbon with N-methylpyrrole, 5b, at 77 K generates the N-methyl-3-dehydropyridinium ylid, 6b, which can be trapped with added hydrogen halides or CO2. The addition of CO2 is strong evidence for the ylid 6b rather than cumulene 7. Deuterium and 13C labeling studies demonstrate that 6b rapidly rearranges to the N-methyl-2-dehydropyridinium ylid, 13, by an intermolecular mechanism. Ylid 13 can be trapped with added acids or with O2 to form 1-methyl-2-pyridone.
