Le lithio-2 naphtalène carbonitrile-1 et ses produits de substitutions

Autor:	S. Savard, R. R. Fraser
Rok vydání:	1986
Předmět:	Bicyclic molecule Nitrile Infrared Chemistry Stereochemistry Organic Chemistry General Chemistry Nuclear magnetic resonance spectroscopy Electrophilic aromatic substitution Catalysis Dissociation constant Electrophilic substitution chemistry.chemical_compound Electrophile
Zdroj:	Canadian Journal of Chemistry. 64:621-625
ISSN:	1480-3291 0008-4042
DOI:	10.1139/v86-100
Popis:	Lithiation of 1-naphthonitrile provides the 2-lithio derivative exclusively. Reaction of this intermediate with ten different electrophiles produces 2-substituted derivatives in moderate to good yields. 2-Alkyl-1-naphthonitriles are readily lithiated and further alkylated to provide alkyl substituents modified at the α position. The pKa values for the hydrogen at the 2-position of 1-cyanonaphthalene and 2-methyl-1-cyanonaphthalene have been determined to be 36.3 and 28.5, respectively.
Databáze:	OpenAIRE
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