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

Kazuhiko Takai; Osamu Fujimura; Yasutaka Kataoka; Kiitiro Utimoto

doi:10.1016/S0040-4039(00)95162-1

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

Kazuhiko Takai, Osamu Fujimura, Yasutaka Kataoka, Kiitiro Utimoto

Research output: Contribution to journal › Article › peer-review

39 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 language	English
Pages (from-to)	211-214
Number of pages	4
Journal	Tetrahedron Letters
Volume	30
Issue number	2
DOIs	https://doi.org/10.1016/S0040-4039(00)95162-1
Publication status	Published - 1989
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(00)95162-1

Cite this

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title = "Preparation of alkenyl sulfides and enamines by alkylidenation of carboxylic acid derivatives",

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.",

author = "Kazuhiko Takai and Osamu Fujimura and Yasutaka Kataoka and Kiitiro Utimoto",

year = "1989",

doi = "10.1016/S0040-4039(00)95162-1",

language = "English",

volume = "30",

pages = "211--214",

journal = "Tetrahedron Letters",

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number = "2",

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T1 - Preparation of alkenyl sulfides and enamines by alkylidenation of carboxylic acid derivatives

AU - Takai, Kazuhiko

AU - Fujimura, Osamu

AU - Kataoka, Yasutaka

AU - Utimoto, Kiitiro

PY - 1989

Y1 - 1989

N2 - 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.

AB - 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.

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U2 - 10.1016/S0040-4039(00)95162-1

DO - 10.1016/S0040-4039(00)95162-1

M3 - Article

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 2

ER -

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

Abstract

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