Straightforward and highly efficient catalyst-free regioselective reaction of thiol to β-nitrostyrene: a concise synthesis of vinyl sulfide and nitro sulfide

Cheng Ming Chu, Zhijay Tu, Pohsi Wu, Chieh Chieh Wang, Ju Tsung Liu, Chun Wei Kuo, Yu Hsuan Shin, Ching Fa Yao

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

Under catalyst-free reaction conditions, solvent-mediated addition of thiol 2 to β-nitrostyrene 1 proceeded with regioselective control to afford either adduct 3 or vinyl sulfide 4 in good to excellent yield. Thermodynamic and autocatalytic reaction mechanisms were proposed to rationalize the products thus formed.

Original languageEnglish
Pages (from-to)3878-3885
Number of pages8
JournalTetrahedron
Volume65
Issue number19
DOIs
Publication statusPublished - 2009 May 9

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Sulfides
Thermodynamics
Sulfhydryl Compounds
Catalysts

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Straightforward and highly efficient catalyst-free regioselective reaction of thiol to β-nitrostyrene : a concise synthesis of vinyl sulfide and nitro sulfide. / Chu, Cheng Ming; Tu, Zhijay; Wu, Pohsi; Wang, Chieh Chieh; Liu, Ju Tsung; Kuo, Chun Wei; Shin, Yu Hsuan; Yao, Ching Fa.

In: Tetrahedron, Vol. 65, No. 19, 09.05.2009, p. 3878-3885.

Research output: Contribution to journalArticle

Chu, Cheng Ming ; Tu, Zhijay ; Wu, Pohsi ; Wang, Chieh Chieh ; Liu, Ju Tsung ; Kuo, Chun Wei ; Shin, Yu Hsuan ; Yao, Ching Fa. / Straightforward and highly efficient catalyst-free regioselective reaction of thiol to β-nitrostyrene : a concise synthesis of vinyl sulfide and nitro sulfide. In: Tetrahedron. 2009 ; Vol. 65, No. 19. pp. 3878-3885.
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