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  • Butyl 3-bromo-3H-diazirine-3-carboxylate (7) and 3-bromo-3-phenyl-3H-diazirine exhibit nitrenic reactivity with phenylmagnesium bromide or tetrabutylammonium cyanide. The formation of several N,N?-disubstituted amidines is attributed to the intermediacy of 1-phenyl or 1-cyano-1H-diazirines possessing a singlet imidoylnitrene character at the N2 atom. Most notably, the reaction of 7 with PhMgBr in diethyl ether affords 2-hydroxy-2,2,N-triphenylacetamidine and 2-methyl-5,5-diphenyl-4-phenylamino-2,5-dihydrooxazole, products derived from nitrene insertion to the alpha-C?H bond of ether.
  • Butyl 3-bromo-3H-diazirine-3-carboxylate (7) and 3-bromo-3-phenyl-3H-diazirine exhibit nitrenic reactivity with phenylmagnesium bromide or tetrabutylammonium cyanide. The formation of several N,N?-disubstituted amidines is attributed to the intermediacy of 1-phenyl or 1-cyano-1H-diazirines possessing a singlet imidoylnitrene character at the N2 atom. Most notably, the reaction of 7 with PhMgBr in diethyl ether affords 2-hydroxy-2,2,N-triphenylacetamidine and 2-methyl-5,5-diphenyl-4-phenylamino-2,5-dihydrooxazole, products derived from nitrene insertion to the alpha-C?H bond of ether. (en)
Title
  • Nitrenic reactivity of diazirines
  • Nitrenic reactivity of diazirines (en)
skos:prefLabel
  • Nitrenic reactivity of diazirines
  • Nitrenic reactivity of diazirines (en)
skos:notation
  • RIV/60461373:22310/13:43895609!RIV14-MSM-22310___
http://linked.open...avai/predkladatel
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  • S
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  • 49
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  • 91814
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  • RIV/60461373:22310/13:43895609
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  • nitrene C?H insertion; imidoylnitrenes; 1H-diazirines; 3H-diazirines (en)
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  • GB - Spojené království Velké Británie a Severního Irska
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  • [FA03CEC5F254]
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  • 54
http://linked.open...iv/tvurceVysledku
  • Martinů, Tomáš
  • Linhart, Igor
  • Kolářová, Petra
  • Álvarez Martínez, Ignacio
  • Čmolík, Václav
http://linked.open...ain/vavai/riv/wos
  • 000327285600023
issn
  • 0040-4039
number of pages
http://bibframe.org/vocab/doi
  • 10.1016/j.tetlet.2013.10.001
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  • 22310
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