Unusually Low Barrier to Carbamate C−N Rotation

The barrier for rotation about an N-alkylcarbamate C(carbonyl)−N bond is around 16 kcal/mol. In the case of an N-phenylcarbamate, the rotational barrier is lowered to 12.5 kcal/mol, but with N-(2-pyrimidyl)carbamates the barriers are so low (

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Veröffentlicht in:Journal of organic chemistry 2002-05, Vol.67 (11), p.3949-3952
Hauptverfasser: Deetz, Martin J, Forbes, Christopher C, Jonas, Marco, Malerich, Jeremiah P, Smith, Bradley D, Wiest, Olaf
Format: Artikel
Sprache:eng
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Zusammenfassung:The barrier for rotation about an N-alkylcarbamate C(carbonyl)−N bond is around 16 kcal/mol. In the case of an N-phenylcarbamate, the rotational barrier is lowered to 12.5 kcal/mol, but with N-(2-pyrimidyl)carbamates the barriers are so low (
ISSN:0022-3263
1520-6904
DOI:10.1021/jo025554u