Nucleophilic substitution at an sp2 carbon of vinyl halides with an intramolecular thiolate moiety: synthesis of 2-alkylidenethietanes

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

doi:10.1016/j.tetlet.2008.04.127

Nucleophilic substitution at an sp² carbon of vinyl halides with an intramolecular thiolate moiety: synthesis of 2-alkylidenethietanes

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

^*Corresponding author for this work

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

18 Citations (Scopus)

Abstract

Various 2-alkylidenethietanes were synthesized by intramolecular nucleophilic substitution reactions at an sp² carbon of vinyl halides with thiolate moieties. The reaction pathway of the substitution reactions was confirmed as a very rare S_NVπ mechanism by theoretical and experimental studies.

Original language	English
Pages (from-to)	4125-4129
Number of pages	5
Journal	Tetrahedron Letters
Volume	49
Issue number	26
DOIs	https://doi.org/10.1016/j.tetlet.2008.04.127
Publication status	Published - Jun 23 2008
Externally published	Yes

ASJC Scopus Subject Areas

Biochemistry
Drug Discovery
Organic Chemistry

Keywords

2-Alkylidenethietane
Density functional theory (DFT)
Nucleophilic vinylic substitution
SVπ mechanism

Access to Document

10.1016/j.tetlet.2008.04.127

Cite this

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title = "Nucleophilic substitution at an sp2 carbon of vinyl halides with an intramolecular thiolate moiety: synthesis of 2-alkylidenethietanes",

abstract = "Various 2-alkylidenethietanes were synthesized by intramolecular nucleophilic substitution reactions at an sp2 carbon of vinyl halides with thiolate moieties. The reaction pathway of the substitution reactions was confirmed as a very rare SNVπ mechanism by theoretical and experimental studies.",

keywords = "2-Alkylidenethietane, Density functional theory (DFT), Nucleophilic vinylic substitution, SVπ mechanism",

author = "Lei, {Mao Yi} and Koji Fukamizu and Xiao, {Yong Jun} and Liu, {Wei Min} and Scott Twiddy and Shunsuke Chiba and Kaori Ando and Koichi Narasaka",

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language = "English",

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journal = "Tetrahedron Letters",

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T1 - Nucleophilic substitution at an sp2 carbon of vinyl halides with an intramolecular thiolate moiety

T2 - synthesis of 2-alkylidenethietanes

AU - Lei, Mao Yi

AU - Fukamizu, Koji

AU - Xiao, Yong Jun

AU - Liu, Wei Min

AU - Twiddy, Scott

AU - Chiba, Shunsuke

AU - Ando, Kaori

AU - Narasaka, Koichi

PY - 2008/6/23

Y1 - 2008/6/23

N2 - Various 2-alkylidenethietanes were synthesized by intramolecular nucleophilic substitution reactions at an sp2 carbon of vinyl halides with thiolate moieties. The reaction pathway of the substitution reactions was confirmed as a very rare SNVπ mechanism by theoretical and experimental studies.

AB - Various 2-alkylidenethietanes were synthesized by intramolecular nucleophilic substitution reactions at an sp2 carbon of vinyl halides with thiolate moieties. The reaction pathway of the substitution reactions was confirmed as a very rare SNVπ mechanism by theoretical and experimental studies.

KW - 2-Alkylidenethietane

KW - Density functional theory (DFT)

KW - Nucleophilic vinylic substitution

KW - SVπ mechanism

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

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