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• W1999331213 endingPage "304" @default.
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• W1999331213 abstract "Acid-Catalysed Formation of Imidazoles from 2H-Azirines or Vinylazides and Nitriles The reaction of 2H-azirines with nitriles in the presence of boron trifluoride etherate to yield the corresponding imidazoles is described. 2,3-Diphenyl-2H-azirine (10) gives 2-substituted 4,5-diphenyl imidazoles in moderate bis good yields (see Table 1). The reaction of 10 with acrylonitrile only leads to the formation of 4,5-diphenyl-2-vinylimidazole (17). No products resulting from an addition to the C,C double bond are observed. 2H-Azirine 10 and ethyl cyanoacetate yield the expected imidazole 18 (30%) but also 2-cyanomethyl-4,5-diphenyloxazole (20; 7%) (see Scheme 4). The yield of imidazole formation mainly depends on the substituents in position 2 of the 2H-azirines (see Scheme 6), a change of the substitutents in position 3 having only little influence. The best yields are observed with a phenyl group at C(2) of the 2H-azirines. These observations are in agreement with the occurrence of 1-azaallyl cations formed by ring opening of the 2H-azirines linked to the Lewis acid (boron trifluoride). Similar results are obtained with the corresponding vinyl azides with the exception of 1-azido-1-phenylethylene (28). Whereas the corresponding 3-phenyl-2H-azirine (24) gives 2,4-diphenylimidazole (33; Scheme 6) in the presence of benzonitrile and boron trifluoride etherate, the azide 28 yields only acetanilide (86%). In the presence of triethyloxonium tetrafluoroborate 2H-azirines and benzonitrile react to yield the corresponding 1-ethylimidazoles (see Scheme 9). This again demonstrates that 1-azaallyl cations must be intermediates which react with the nitrile presumably in a Ritter type reaction. 13C-NMR. spectra of 2H-azirines are also reported (Table 2)." @default.
• W1999331213 created "2016-06-24" @default.
• W1999331213 creator A5018819101 @default.
• W1999331213 creator A5076007123 @default.
• W1999331213 date "1978-01-25" @default.
• W1999331213 modified "2023-10-17" @default.
• W1999331213 title "Zur Imidazolbildung aus 2<i>H</i>-Azirinen bzw. Vinylaziden und Nitrilen unter Säurekatalyse" @default.
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• W1999331213 doi "https://doi.org/10.1002/hlca.19780610126" @default.
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