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2005
Triazole derivatives
R 0280
β-Acylvinyl Anion and Dianion Equivalents: Lithiation of 1-[(2EZ)-3-ChloroPreparation and Elaboration of 1-(2-Oxira01- 111 prop-2-enyl]-1H-1,2,3-benzotriazole:
nylvinyl)-1H-benzotriazoles. — LDA-mediated treatment of 3-chloroalkylbenzotriazole with carbonyl compounds leads to different products depending on the conditions
used. Thus, in the absence of HMPA preferred or exclusive attack at the C-Btr terminus
takes place whereas in the presence of HMPA regiospecific lithiation/substitution at the
C-Cl terminus is possible giving (oxiranylvinyl)benzotriazoles. The latter regiospecifically react with alkyl iodides to afford epoxides of type (XVII). Acidic hydrolysis of
the (oxiranylvinyl)benzotriazoles leads to α,β-unsaturated γ-hydroxyaldehydes or -ketones indicating that 3-chloroalkylbenzotriazole is an useful β-acylvinyl anion and dianion equivalent. — (KATRITZKY*, A. R.; MANJU, K.; GROMOVA, A. V.; STEEL,
P. J.; J. Org. Chem. 69 (2004) 18, 6018-6023; Dep. Chem., Univ. Fla., Gainesville, FL
32611, USA; Eng.) — Jannicke
2005
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