The Birch reduction-dialkylation reaction. Scope and limitations

Tetrahedron Letters

Volumn 47, Issue 6, 2006, Pages 973-976

  Castanedo, Ricardo ^a   Covarrubias Zúñiga, Adrián ^a   Maldonado, Luis A ^a  

^a UNIVERSIDAD NACIONAL AUTÓNOMA DE MÉXICO   (Mexico)

Author keywords

Birch reduction; Dialkylation; Primary and secondary alkyl bromides; Substituted benzoic acids

Indexed keywords

5 BROMO 2 METHYL 2 PENTENE; ALLYL BROMIDE; AROMATIC CARBOXYLIC ACID; BETA PHENETHYL BROMIDE; BROMINE DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; BIRCH REDUCTION; BROMINATION; CHEMICAL REACTION; DEHALOGENATION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 30344432118     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.11.138     Document Type: Article

References (10)

1. J.A. Guzmán, R. Castanedo, and L.A. Maldonado Synth. Commun. 21 1991 1001 1012
2. Unpublished results.
3. 1H NMR and/or GC. Note: In the case of methoxy substituted benzoic acids, careful acidification with cold acid and rapid extraction is crucial to avoid hydrolysis of the acid sensitive methoxy enol ethers present in the products. For alkyl substituted benzoic acids, the usual acidification and workup can be followed.
4. 1H NMR spectrum. This second method of analysis was especially useful when important amounts of monoalkylated product were obtained.
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