Deuterium studies in the disproportionation of pyrimido[4,5-b]quinolinium salts

Mechanism of pseudobase disproportionation. Kinetics and mechanism of the reaction of the pseudobases of 2-(substituted-benzyl)-5-nitroisoquinolinium cations with the 2-methylisoquinolinium cation

“…The product spectrum clearly indicated a mixture of 10, X = 4-CN, and 11. Repetition of this experiment in basic D2O, and also the corresponding reaction of the l-deuterio-2-(4-cyanobenzyl)-5-nitroisoquinolinium (14) and 2-methylisoquinolinium cations in H20, indicated that there was no detectable incorporation of solvent hydrogen at C-l of the l,2-dihydro-2methylisoquinoline product. Thus direct transfer of hydrogen occurs from C-l of the N-(4-cyanobenzyl)isoquinoline derivative to C-l of 9.…”