Journal of Organic Chemistry p. 5164 - 5170 (1983)
Update date:2022-08-03
Topics:
Phan, Xuan T.
Shannon, Paul J.
The photoinduced dehydrochlorination, in methanol, of N-chloro-N-alkyl amides with one substitient at the α position to nitrogen gave good yields of N-(α-methoxyalkyl) amides and the parent amides as secondary products.N-Chloro amides disubstituted at the α position gave mostly parent amides.In most cases no products resulting from 1,5 hydrogen transfer of amidyl radicals were observed.The quantum yields of decomposition of N-chloro-N-methylpentanamide (1a) were significantly greater than unity, indicative of a chain process for dehydrochlorination.The reaction was affected by the solvent, addition of base or radical inhibitors, concentration of N-chloro amide, light intensity, and irradiation wavelenght.
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