Heterocycles p. 865 - 870 (1998)
Update date:2022-09-26
Topics:
Endo, Katsuya
Hirayama, Kaoru
Aota, Yuko
Seya, Kazuhiko
Asakura, Hirotatsu
Hisamichi, Kanehiko
Proline was decarboxylated quantitatively to Δ1-pyrroline on photoirradiation in the presence of rose bengal, while its methyl ester yielded an equimolar mixture of Δ1- and Δ5-pyrroline-2-carboxylic acid methyl esters. The decarboxylation of proline took place under either an aerobic (O2 bubbling) or an anaerobic (N2 bubbling) conditions, and under the latter condition, extent of the reaction depended on the amount of rose bengal employed. These results imply mechanistically that the reaction is the Type I photooxidation, indicating a new type of oxidative stress to natural secondary amines.
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