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Lithiation of 1‐benzylimidazole. A hypothesis on the regioselectivity of the electrophilic attacks on the lithiated species
Author(s) -
MorenoMañas M.,
Bassa J.,
Lladó N.,
Pleixats R.
Publication year - 1990
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570270335
Subject(s) - chemistry , regioselectivity , electrophile , halide , steric effects , alkyl , carbon atom , medicinal chemistry , electrophilic substitution , organic chemistry , combinatorial chemistry , catalysis
Sequential lithiations of 1‐benzylimidazole, 1 , and of 1‐benzyl‐1,2,4‐triazole, 2 , followed by treatment with electrophiles others than alkyl halides result in reactions at C‐2. However, benzyl halides and, to a certain extent, iodomethane react at the N ‐benzyl carbon atom. An explanatory hypothesis based on steric ortho effects is advanced.