Concerted nucleophilic substitution reactions at vinylic carbons

Shunsuke Chiba; Kaori Ando; Koichi Narasaka

doi:10.1055/s-0029-1217752

Concerted nucleophilic substitution reactions at vinylic carbons

Shunsuke Chiba, Kaori Ando, Koichi Narasaka^*

^*Corresponding author for this work

Research output: Contribution to journal › Review article › peer-review

36 Citations (Scopus)

Abstract

In this account, recent advances on nucleophilic substitution reactions at sp(2) hybridized carbons of lithium alkylidene carbenoids and simple vinyl halides are described. 1 Introduction 2 Nucleophilic Substitution Reactions of Lithium Alkylidene Carbenoids 2.1 Reactions of Dibromoalkenols with Alkyllithiums 2.2 Reactions of Alkylidene Carbenoids with Intramolecular Carbanions: Synthesis of Indenes and Dihydronaphthalenes 3 Nucleophilic Substitution Reactions of Vinyl Halides 3.1 With Oxygen Nucleophiles 3.2 With Nitrogen Nucleophiles 3.3 With Carbon Nucleophiles 3.4 With Sulfur Nucleophiles 4 Conclusion.

Original language	English
Pages (from-to)	2549-2564
Number of pages	16
Journal	Synlett
Issue number	16
DOIs	https://doi.org/10.1055/s-0029-1217752
Publication status	Published - 2009
Externally published	Yes

ASJC Scopus Subject Areas

Organic Chemistry

Keywords

Cyclizations
Density functional theory
Lithium alkylidene carbenoids
Nucleophilic substitutions
Vinyl halides

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10.1055/s-0029-1217752

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title = "Concerted nucleophilic substitution reactions at vinylic carbons",

abstract = "In this account, recent advances on nucleophilic substitution reactions at sp(2) hybridized carbons of lithium alkylidene carbenoids and simple vinyl halides are described. 1 Introduction 2 Nucleophilic Substitution Reactions of Lithium Alkylidene Carbenoids 2.1 Reactions of Dibromoalkenols with Alkyllithiums 2.2 Reactions of Alkylidene Carbenoids with Intramolecular Carbanions: Synthesis of Indenes and Dihydronaphthalenes 3 Nucleophilic Substitution Reactions of Vinyl Halides 3.1 With Oxygen Nucleophiles 3.2 With Nitrogen Nucleophiles 3.3 With Carbon Nucleophiles 3.4 With Sulfur Nucleophiles 4 Conclusion.",

keywords = "Cyclizations, Density functional theory, Lithium alkylidene carbenoids, Nucleophilic substitutions, Vinyl halides",

author = "Shunsuke Chiba and Kaori Ando and Koichi Narasaka",

year = "2009",

doi = "10.1055/s-0029-1217752",

language = "English",

pages = "2549--2564",

journal = "Synlett",

issn = "0936-5214",

publisher = "Georg Thieme Verlag",

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TY - JOUR

T1 - Concerted nucleophilic substitution reactions at vinylic carbons

AU - Chiba, Shunsuke

AU - Ando, Kaori

AU - Narasaka, Koichi

PY - 2009

Y1 - 2009

N2 - In this account, recent advances on nucleophilic substitution reactions at sp(2) hybridized carbons of lithium alkylidene carbenoids and simple vinyl halides are described. 1 Introduction 2 Nucleophilic Substitution Reactions of Lithium Alkylidene Carbenoids 2.1 Reactions of Dibromoalkenols with Alkyllithiums 2.2 Reactions of Alkylidene Carbenoids with Intramolecular Carbanions: Synthesis of Indenes and Dihydronaphthalenes 3 Nucleophilic Substitution Reactions of Vinyl Halides 3.1 With Oxygen Nucleophiles 3.2 With Nitrogen Nucleophiles 3.3 With Carbon Nucleophiles 3.4 With Sulfur Nucleophiles 4 Conclusion.

AB - In this account, recent advances on nucleophilic substitution reactions at sp(2) hybridized carbons of lithium alkylidene carbenoids and simple vinyl halides are described. 1 Introduction 2 Nucleophilic Substitution Reactions of Lithium Alkylidene Carbenoids 2.1 Reactions of Dibromoalkenols with Alkyllithiums 2.2 Reactions of Alkylidene Carbenoids with Intramolecular Carbanions: Synthesis of Indenes and Dihydronaphthalenes 3 Nucleophilic Substitution Reactions of Vinyl Halides 3.1 With Oxygen Nucleophiles 3.2 With Nitrogen Nucleophiles 3.3 With Carbon Nucleophiles 3.4 With Sulfur Nucleophiles 4 Conclusion.

KW - Cyclizations

KW - Density functional theory

KW - Lithium alkylidene carbenoids

KW - Nucleophilic substitutions

KW - Vinyl halides

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U2 - 10.1055/s-0029-1217752

DO - 10.1055/s-0029-1217752

M3 - Review article

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EP - 2564

JO - Synlett

JF - Synlett

IS - 16

ER -

Concerted nucleophilic substitution reactions at vinylic carbons

Abstract

ASJC Scopus Subject Areas

Keywords

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