Studies on sulfenamides. II. Oxidation of 2- and 4'-substituted benzenesulfenanilides with lead dioxide.

• 佐用 博照

• 森 浩一

• 道田 隆

抄録

2-and 4'-Substituted benzenesulfenanilidyl radicals were generated by the oxidations of benzenesulfenanilides (4'-OMe (1a), 4'-Me (1b), 4'-Cl (1c), 4'-H (1d)) and 2-nitrobenzene-sulfenanilides (4'-OMe (3a), 4'-Me (3b), 4'-Cl (3c), 4'-H (3d)) with lead dioxide, and their electron spin resonance (ESR) and visible spectra were investigated. The radicals generated from 1a, 1b, 3a, and 3b in benzene were fairly stable and gave well-resolved ESR spectra, whereas those from 1c, 1d, 3c, and 3d were less stable and decomposed thoroughly in an hour. The oxidations of 1a and 1b in benzene gave the corresponding 2, 7-disubstituted phenazines as the final products, whereas those of 1c, 1d, 3a-d did not. The oxidations of 3a-d in acetonitrile containing 1% CF₃COOH and 1% (CF₃CO)₂O gave the corresponding phenazines and N-(2-nitrophenylthio) acetamide (6). The formation of 6 was interpreted in terms of acetamidation of the sulfenylium ion.

収録刊行物

• ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ

  ＣＨＥＭＩＣＡＬ　＆　ＰＨＡＲＭＡＣＥＵＴＩＣＡＬ　ＢＵＬＬＥＴＩＮ 27 (2), 351-356, 1979

  公益社団法人 日本薬学会

キーワード

• acetamidation

詳細情報

• CRID: 1390282679147307008
• NII論文ID: 110003623613
• NII書誌ID: AA00602100
• DOI: 10.1248/cpb.27.351
• COI: 1:CAS:528:DyaE1MXktVGhsr4%3D
• ISSN: 13475223
• ISSN: 00092363
• Web Site: http://www.jstage.jst.go.jp/article/cpb1958/27/2/27_2_351/_pdf
• Web Site: https://search.jamas.or.jp/link/ui/1979130624
• 本文言語コード: en
• データソース種別:
  • JaLC
  • Crossref
  • CiNii Articles
• 抄録ライセンスフラグ: 使用不可