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70350489499
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'), the fully delocalized structure III' prevails over the imidazol-5ylidene resonance form III (18). These structures fit into the definition of mesoionic compounds (19, 20) and could be named 5-dehydroimidazolium ylides.
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'), the fully delocalized structure III' prevails over the imidazol-5ylidene resonance form III (18). These structures fit into the definition of mesoionic compounds (19, 20) and could be named 5-dehydroimidazolium ylides.
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19
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70350516823
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32
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70350507529
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Preparation methods and spectroscopic data for compounds 6 through 11 and computational details are available as supporting material on Sdence Online.
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Preparation methods and spectroscopic data for compounds 6 through 11 and computational details are available as supporting material on Sdence Online.
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34
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70350520560
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Because of the counterion (H)WT, where X is CL or Br, two equivalents of base are needed.
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Because of the counterion (H)WT, where X is CL or Br), two equivalents of base are needed.
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36
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33750183982
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39
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70350510364
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note
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The addition of LiBr or [12]crown-4 to a benzene solution of aNHC 9 does not catalyze the rearrangement into 8. In contrast, the addition of both LiBr and [12]crown-4 induces the transformation of 9 into 8 at room temperature, suggesting that the free bromide anion facilitates the proton transfer, through hydrogen bonding, in agreement with previous works (33).
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40
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70350501557
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2 adducts (42, 43) have recently attracted considerable interest.
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2 adducts (42, 43) have recently attracted considerable interest.
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44
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70350491450
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note
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We thank NIH (grant RO1 GM 68825) and the Deutsche Forschungsgemeinschaft for financial support of this work and the Consejo Nacional de Ciencia y Tecnología (EAP.) and Alexander von Humboldt Foundation (P.P.) for postdoctoral fellowships. Metrical data for the solid-state structures of 6 (BO, 8, 9, and 10 are available free of charge from the Cambridge Cryslallographic Data Centre under reference numbers CCDC-735754, CCDC-735755, CCDC-735756, and CCDC-744123, respectively.
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