Optional Site Selectivity in the Metalation of o- and p-Anisidine through Matching of Reagents with Neighboring Groups
N-Protected o- and p-anisidines (2- and 4-methoxyanilines) undergo a hydrogen/metal exchange at the position adjacent to either the oxygen or nitrogen atom depending on what organometallic base is employed. These synthetically useful findings support previous views about neighboring group/reagent interactions. [on SciFinder (R)]
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Maggi, R., & Schlosser, M. (1996). Optional Site Selectivity in the Metalation of o- and p-Anisidine through Matching of Reagents with Neighboring Groups. The Journal of Organic Chemistry, 61(16), 5430–5434. https://doi.org/10.1021/jo9604550
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1996
61
16
5430
5434
CAN 125:195123 25-19 Benzene, Its Derivatives, and Condensed Benzenoid Compounds Institut de Chimie Organique,Universite,Lausanne-Dorigny,Switz. Journal 0022-3263 written in English. 79-44-7 (N,N-Dimethylcarbamoyl chloride); 88-10-8 (N,N-Diethylcarbamoyl chloride); 90-04-0 (o-Anisidine); 104-94-9 (p-Anisidine); 107-31-3 (Methyl formate); 18437-68-8; 154150-18-2 Role: RCT (Reactant), RACT (Reactant or reagent) (optional site selectivity in the lithiation of o- and p-anisidine through matching of reagents with neighboring groups); 7160-02-3P; 56015-84-0P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (optional site selectivity in the lithiation of o- and p-anisidine through matching of reagents with neighboring groups); 83996-83-2P; 180690-82-8P; 180690-83-9P; 180690-84-0P; 180690-85-1P; 180690-86-2P; 180690-87-3P; 180690-88-4P; 180690-89-5P; 180690-90-8P; 180690-91-9P; 180690-92-0P; 180690-93-1P; 180690-94-2P; 180690-95-3P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of)
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