A novel ambident reactivity of azolylacroleins |
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| Authors: | Ildikó Nagy Zsuzsanna Riedl Orsolya Egyed Imre Pápai |
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| Institution: | Chemical Research Center, H-1025 Budapest, Pusztaszeri út 59, Hungary |
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| Abstract: | Reaction of azolylacroleins with phosphoranes bearing a conjugated double bond was found to yield either azolyltrienes in a Wittig reaction, or to undergo cyclization to a dihydrobenzene containing the azole substituent. Transformation with an aza-Wittig reagent gave tetrazolylpyridines. The ambident reactivity was found to be dependent on the substituent of the phosphorane, which was rationalized by ab initio (DFT) calculation of the atomic charges of the reaction centres. |
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| Keywords: | Azolyltriene Wittig reaction Phosphorane Ab initio calculation |
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