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Synthesis 2002(5): 0674-0680
DOI: 10.1055/s-2002-23546
DOI: 10.1055/s-2002-23546
PAPER
© Georg Thieme Verlag Stuttgart · New York
Base-mediated Reaction of Quaternary Ammonium Salts with Nitroarenes - Their Useful Functionalization via Vicarious Nucleophilic Substitution (VNS)
Further Information
Received
10 January 2002
Publication Date:
02 April 2002 (online)
Publication History
Publication Date:
02 April 2002 (online)
Abstract
Ammonium ylides generated from ammonium salt 1a-e with a base react with derivatives of 3-nitropyridine 2a-c and 2-nitrothiophene (3) to form products of vicarious nucleophilic substitution (VNS) 7, 8, or 9 respectively. The products of VNS 10, 11, or 12 are also produced from the corresponding ammonium salts, a base and 4-chloro-nitrobenzene (4), nitrobenzene (5), or 1-nitronaphthalene (6), respectively. In a few products, an exchange of alkoxy group 7c or substitution of chlorine by alkoxyl 8a,b occured.
Key words
ylides - nucleophilic aromatic substitution - nitriles - esters - amides
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