Nucleophilic substitution reaction at an sp2 carbon of vinyl halides with an intramolecular thiol moiety: synthesis of thio-heterocycles

Mao Yi Lei; Yong Jun Xiao; Wei Min Liu; Koji Fukamizu; Shunsuke Chiba; Kaori Ando; Koichi Narasaka

doi:10.1016/j.tet.2009.06.078

Nucleophilic substitution reaction at an sp² carbon of vinyl halides with an intramolecular thiol moiety: synthesis of thio-heterocycles

Mao Yi Lei, Yong Jun Xiao, Wei Min Liu, Koji Fukamizu, Shunsuke Chiba, Kaori Ando, Koichi Narasaka^*

^*Corresponding author for this work

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

35 Citations (Scopus)

Abstract

This article presents a full account of intramolecular vinylic substitution reactions of bromoalkenes having an acetylthio moiety, which give sulfur-containing heterocycles such as dihydrothiophene, tetrahydrothiopyran, and 2-alkylidenethietane derivatives. The reaction pathways of the substitution reactions were investigated by theoretical and experimental studies.

Original language	English
Pages (from-to)	6888-6902
Number of pages	15
Journal	Tetrahedron
Volume	65
Issue number	34
DOIs	https://doi.org/10.1016/j.tet.2009.06.078
Publication status	Published - Aug 22 2009
Externally published	Yes

ASJC Scopus Subject Areas

Biochemistry
Drug Discovery
Organic Chemistry

Keywords

Density functional theory (DFT)
Nucleophilic vinylic substitution
SVσ and SVπ mechanisms
Sulfur-containing heterocycles

Access to Document

10.1016/j.tet.2009.06.078

Cite this

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title = "Nucleophilic substitution reaction at an sp2 carbon of vinyl halides with an intramolecular thiol moiety: synthesis of thio-heterocycles",

abstract = "This article presents a full account of intramolecular vinylic substitution reactions of bromoalkenes having an acetylthio moiety, which give sulfur-containing heterocycles such as dihydrothiophene, tetrahydrothiopyran, and 2-alkylidenethietane derivatives. The reaction pathways of the substitution reactions were investigated by theoretical and experimental studies.",

keywords = "Density functional theory (DFT), Nucleophilic vinylic substitution, SVσ and SVπ mechanisms, Sulfur-containing heterocycles",

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T2 - synthesis of thio-heterocycles

AU - Lei, Mao Yi

AU - Xiao, Yong Jun

AU - Liu, Wei Min

AU - Fukamizu, Koji

AU - Chiba, Shunsuke

AU - Ando, Kaori

AU - Narasaka, Koichi

PY - 2009/8/22

Y1 - 2009/8/22

N2 - This article presents a full account of intramolecular vinylic substitution reactions of bromoalkenes having an acetylthio moiety, which give sulfur-containing heterocycles such as dihydrothiophene, tetrahydrothiopyran, and 2-alkylidenethietane derivatives. The reaction pathways of the substitution reactions were investigated by theoretical and experimental studies.

AB - This article presents a full account of intramolecular vinylic substitution reactions of bromoalkenes having an acetylthio moiety, which give sulfur-containing heterocycles such as dihydrothiophene, tetrahydrothiopyran, and 2-alkylidenethietane derivatives. The reaction pathways of the substitution reactions were investigated by theoretical and experimental studies.

KW - Density functional theory (DFT)

KW - Nucleophilic vinylic substitution

KW - SVσ and SVπ mechanisms

KW - Sulfur-containing heterocycles

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JO - Tetrahedron

JF - Tetrahedron

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