ISOLATION AND CHARACTERIZATION OF A PYRIMIDINE SULFENIC ACID VIA SCISSION OF SULFUR-SULFUR BOND IN METHYL ANALOG OF BIS(4-THIOURIDINE) DISULFIDE

It has been established that bis(1-β-D-ribofuranosy1-4-thiouracil) disulfide and its methyl analog are hydrolyzed almost quantitatively in alkali to the corresponding thiones and sulfenic acids in 1:1 molar ratios. 1-Methyluracil-4-sulfenic acid was isolated and characterized as its silver salt. Uridine-4-sulfenic acid was identified by the similarity of its uv absorption spectra with those of its 1-methyl analog. Some of the properties of the sulfenic acid derivatives are reported. The cleavage of the disulfides in acid, on the other hand, gives quantitative formation of the corresponding thiones and uracil derivatives. © 1969, American Chemical Society. All rights reserved.