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Flow NMR 277 an enormous paf would be required to effect simple proton removal. A possible alternative route is the conversion of the carbonyl compound to the protonated Schiff base. r2c=o + rnh2 + h+ ^r2c=nhr + h2o Such species do indeed have reactive methylene groups,37 and can be present in reasonable concentrations in neutral solution. Further work is needed to determine the importance of this alternative form of activation.(37) (a) M. L. Bender and A.

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Low-temperature flow N M R has been used to investigate [he reaction of 2,4.6-trinitroaiiisolc with secondary amines in 50% Mc,SO-50% MeOH solvent. I t is found that thc v complex on thc substitution pathway ( i c , by attack of thc amine at C , ) is formed in ;I very fast reaction and that it is relatively stable under thcsc conditions. The sjstcm does not yield the cxpcctcd substitution. houevcr. Instead a side reaction involving the solvent methanol occurs yielding the I ,I-dimcthoxy Mciscnhcinicr complex.

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