Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Organic Photochemical Reactions. XXX. Photoreactions of N,N-Dimethylpyruvamide in Methanol and Ethanol
Kensuke ShimaKimiko TanabeShinpei FurukawaJouji SaitoKazuhiro Shirahashi
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1984 Volume 57 Issue 6 Pages 1515-1517

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Abstract

The photoreactions of N,N-dimethylpyruvamide (DMPA) in methanol and ethanol were investigated. Irradiation of DMPA in methanol gave three products (3,5-dimethyl-4-oxazolidinone, 2-hydroxy-N-methyl-N-(methoxymethyl)propanamide, and 2,3-dihydroxy-2,3-dimethyl-N,N,N′-trimethyl-N′-(methoxymethyl)-butanediamide) in good yields. The product distribution was dependent on the concentration of DMPA and methanol. Similarly, irradiation of DMPA in ethanol gave three products (3,5-dimethyl-4-oxazolidinone, 2-hydroxy-N-methyl-N-(ethoxymethyl)propanamide, and 2,3-dihydroxy-2,3-dimethyl-N,N,N′-trimethyl-N′-(ethoxymethyl)butanediamide). The mechanism for the formation of these products is discussed.

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