Nature of N-S bond cleavage of 2,3-dihydro-2,2-dimethyl-7-benzofuranyl (di-n-butylaminosulfenyl) (methyl)carbamate.

Abstract

The cleavage of the N-S bond in 2,3-dihydro-2,2-dimethyl-7-benzofuranyl (di-n-butylaminosulfenyl) (methyl)carbamate was examined in different buffer solutions (hydrolysis), in buffer solution containing sulfhydryl reagents (thiolysis) and on thin-layer chromatographic plates. In buffer solution and on thin-layer plates, N-S bond cleavage readily occurred to give carbofuran as a major product, with minor amounts of bis-carbofuran-N,N'-disulfide and -trisulfide. The hydrolysis reaction in buffer proceeded with first-order kinetics. Significant amounts of an unknown polar compound were obtained in buffer solution and on thin-layer plates. In the presence of excess cysteine and glutathione at pH 7.0, thiolytic N-S bond cleavage occurred with first-order kinetics to give carbofuran as the sole identifiable product. At pH 5.0, three minor products were obtained along with carbofuran.