The Photochemistry of Carbamates, I

Abstract

The photodecomposition of 4-dimethylamino-3,5-xylyl-N-methyl carbamate (Zectran) in aerated and degassed solution has been carried out. Three major photoproducts were detected and characterized to be: 4-dirnethylamino-3,5-dimethyl Rhenol, 4-hydroxy-2,6-dimethyl-N-methyl benzamide and 4-monomethylamino-3,5-xylyl-N-methyl carbamate. The phenol and benzamide products suggest that one of the pathways of photodecomposition of Zectran is via a photo-Fries rearrangement. The ortho-benzamide (5-dimethylamino-4,6-dimethyl-2-hydroxy-N-methyl benzamide) which could also be expected to occur in a photo-Fries reaction, was not observed. The excitation wavelength was > 296.7 nm, i.e. radiation available in the solar spectrum. Thus the products observed in this study may be expected to occur in the environment as a result of the action of sunlight on Zectran.