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7743180 
Journal Article 
Metallation and functionalization of 1-allenylpyrrole 
Tarasova, OA; Taherirastgar, F; Verkruijsse, HD; Malkina, AG; Brandsma, L; Trofimov, BA 
1996 
1 
Recueil des Travaux Chimiques des Pays-Bas
ISSN: 0165-0513 
Koninklijke Nederlandse Chemische Vereniging 
AMSTERDAM 
115 
2 
145 
English 
WOS:A1996TW76100006 
1-Allenylpyrrole is lithiated at the α-carbon atom of the allenyl group by n-butyllithium in mixtures of diethyl-ether/hexane or tetrahydrofuran/hexane. Whereas functionalization with trimethylchlorosilane, butyl iodide and dimethyl disulfide gives only allenic derivatives, addition of carbonyl compounds generally leads to mixtures of allenic and acetylenic derivatives. Upon heating its solutions in ether or tetrahydrofuran, Li-allenylpyrrole is slowly transformed into the lithium derivative of 1-(propyn-2-yl)pyrrole. 
1-(propyn-2-yl)pyrrole; n-butyllithium; lithium diisopropylamide; regiochemistry