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Synlett 2009(16): 2549-2564
DOI: 10.1055/s-0029-1217752
DOI: 10.1055/s-0029-1217752
ACCOUNT
© Georg Thieme Verlag
Stuttgart ˙ New York
Concerted Nucleophilic Substitution Reactions at Vinylic Carbons
Further Information
Received
25 February 2009
Publication Date:
09 September 2009 (online)
Publication History
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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