Preparation of alkenyl sulfides and enamines by alkylidenation of carboxylic acid derivatives

Kazuhiko Takai, Osamu Fujimura, Yasutaka Kataoka, Kiitiro Utimoto

Research output: Contribution to journalArticle

37 Citations (Scopus)

Abstract

Treatment of S-alkyl thioesters with a reagent prepared from RCHBr2, Zn, TiCl4, and TMEDA in THF at 25°C gives Z-alkenyl sulfides selectively in good to excellent yields. Using the alkylidenation method, ketene dithioacetals and enamines are produced from 1,3-dithian-2-one and amides, respectively.

Original languageEnglish
Pages (from-to)211-214
Number of pages4
JournalTetrahedron Letters
Volume30
Issue number2
DOIs
Publication statusPublished - 1989
Externally publishedYes

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Sulfides
Carboxylic Acids
Amides
Derivatives
ketene
titanium tetrachloride
phenyllithium

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Preparation of alkenyl sulfides and enamines by alkylidenation of carboxylic acid derivatives. / Takai, Kazuhiko; Fujimura, Osamu; Kataoka, Yasutaka; Utimoto, Kiitiro.

In: Tetrahedron Letters, Vol. 30, No. 2, 1989, p. 211-214.

Research output: Contribution to journalArticle

Takai, Kazuhiko ; Fujimura, Osamu ; Kataoka, Yasutaka ; Utimoto, Kiitiro. / Preparation of alkenyl sulfides and enamines by alkylidenation of carboxylic acid derivatives. In: Tetrahedron Letters. 1989 ; Vol. 30, No. 2. pp. 211-214.
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