Abstract
Phototransposition chemistry of pyridine and substituted pyridines in the vapor phase
Highlights
They suggested the interconversion of 1 and 2 may occur via a radical methylation–demethylation process
AP-1 can undergoing opening by three distinct bond cleavage pathways resulting in the formation pf Dewar-pyridines DP-1-2,5, DP-1-N,4, and DP-9-2,5
Irradiation of each methylpyridine or each cyanopyridine in the vapor phase at 254 nm resulted in the formation of the other two isomers as primary products
Summary
They suggested the interconversion of 1 and 2 may occur via a radical methylation–demethylation process. Roebke[5] suggested a mechanism involving an azaprismane intermediate formed from a Dewar-pyridine as a reasonable reaction pathway for the observed rearrangement. Bond cleavage and rearomatization would yield that starting pyridine 1 and 4-methylpyridine 2, the other observed product.
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