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Synlett 2009(16): 2549-2564  
DOI: 10.1055/s-0029-1217752
ACCOUNT
© Georg Thieme Verlag Stuttgart ˙ New York

Concerted Nucleophilic Substitution Reactions at Vinylic Carbons

Shunsuke Chibaa, Kaori Andob, Koichi Narasaka*a
a Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore
Fax: +6567911961; e-Mail: narasaka@ntu.edu.sg;
b Department of Chemistry, Faculty of Engineering, Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan
Further Information

Publication History

Received 25 February 2009
Publication Date:
09 September 2009 (online)

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Abstract

In this account, recent advances on nucleophilic substitution reactions at sp² 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

Key words

nucleophilic substitutions - lithium alkylidene carbenoids - vinyl halides - cyclizations - density functional theory

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