Electrosynthesis of hetero-hetero atom bonds. 2. An efficient preparation of (2-benzothiazolyl)- and thiocarbamoylsulfenamides by electrolytic cross-coupling reaction of 2-mercaptobenzothiazole, bis(2-benzothiazolyl) disulfide, and/or bis(dialkylthiocarbamoyl) disulfides with various amines

Sigeru Torii, Hideo Tanaka, Masasi Ukida

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19 Citations (Scopus)

Abstract

Two series of sulfenamides bearing 2-benzothiazolyl and thiocarbamoyl moieties were synthesized smoothly by electrolytic cross-coupling of either 2-mercaptobenzothiazole (3), bis(2-benzothiazolyl) disulfide (4) or bis(dialkylthiocarbamoyl) disulfides (5) with various amines in N,N-dimethylformamide. Electrolysis was carried out under constant voltages of 2-3 V (0.95-1.20 V vs. SCE) in an undivided cell, fitted with two platinum and/or two stainless steel Sus 27 electrodes. Direct electrosynthesis of thiocarbamoylsulfenamides (2) from dialkylamines and carbon disulfide was also accomplished in 81-96% yields.

Original languageEnglish
Pages (from-to)3223-3227
Number of pages5
JournalJournal of Organic Chemistry
Volume43
Issue number16
Publication statusPublished - 1978

ASJC Scopus subject areas

  • Organic Chemistry

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