TY - JOUR
T1 - Lithiation of 1‐benzylimidazole. A hypothesis on the regioselectivity of the electrophilic attacks on the lithiated species
AU - Moreno‐Mañas, M.
AU - Bassa, J.
AU - Lladó, N.
AU - Pleixats, R.
PY - 1990/1/1
Y1 - 1990/1/1
N2 - 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. Copyright © 1990 Journal of Heterocyclic Chemistry
AB - 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. Copyright © 1990 Journal of Heterocyclic Chemistry
U2 - 10.1002/jhet.5570270335
DO - 10.1002/jhet.5570270335
M3 - Article
VL - 27
SP - 673
EP - 678
JO - Journal of Heterocyclic Chemistry
JF - Journal of Heterocyclic Chemistry
SN - 0022-152X
IS - 3
ER -