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  • β-Acylvinyl Anion and Dianion Equivalents: Lithiation of1-[(2EZ)-3-Chloroprop-2-enyl]-1H-1,2,3-benzotriazole: Preparationand Elaboration of 1-(2-Oxiranylvinyl)-1H-benzotriazoles
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  • The allyllithium generated from 1-[(2EZ)-3-chloroprop-2-enyl]-1H-1,2,3-benzotriazole (5) and LDA,in the presence of HMPA, reacts with enolizable and nonenolizable carbonyls solely at the CClterminus to give 1-(2-oxiranylvinyl)benzotriazoles 6a−g in 61−82% yields. Allyllithiums generatedfrom 6a,c reacted exclusively at the CBt terminus to give 10a−d in 68−88% yields. Acidic hydrolysisof (oxiranylvinyl)benzotriazoles 6a−g and 10a−d provided 4-hydroxyalk-2-en-1-one derivatives12a,b,c,e,g, 13a−d, and furan 14 in 54−86% yields.
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