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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Bibliographic Details
Published in:Journal of organic chemistry 2002-05, Vol.67 (11), p.3949-3952
Main Authors: Deetz, Martin J, Forbes, Christopher C, Jonas, Marco, Malerich, Jeremiah P, Smith, Bradley D, Wiest, Olaf
Format: Article
Language:English
Subjects:
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Organic chemistry
Preparations and properties
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Description
Summary: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