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

Research output: Contribution to journalArticle

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

Fingerprint

Disulfides
Amines
Bearings (structural)
Carbon Disulfide
Dimethylformamide
Atoms
Stainless Steel
Platinum
Electrolysis
Electrodes
Electric potential
captax
sulfenamide

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

@article{4e9b9bf55f63410381d0829039eee32b,
title = "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",
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.",
author = "Sigeru Torii and Hideo Tanaka and Masasi Ukida",
year = "1978",
language = "English",
volume = "43",
pages = "3223--3227",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "16",

}

TY - JOUR

T1 - 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

AU - Torii, Sigeru

AU - Tanaka, Hideo

AU - Ukida, Masasi

PY - 1978

Y1 - 1978

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=4544245655&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=4544245655&partnerID=8YFLogxK

M3 - Article

AN - SCOPUS:4544245655

VL - 43

SP - 3223

EP - 3227

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 16

ER -