Journal
TETRAHEDRON LETTERS
Volume 52, Issue 17, Pages 2181-2184Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2010.11.121
Keywords
Nitrone; 1,3-Dipolar cycloaddition; Density functional calculations; Transition states; Ring strain
Categories
Funding
- NSF [CHE-0548209]
- Australian Research Council [DP0985623]
- EPSRC
- Fisons Pharmaceuticals plc
- CSIRO
- ARC Centre of Excellence for Free Radical Chemistry and Biotechnology
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1059084] Funding Source: National Science Foundation
- Australian Research Council [DP0985623] Funding Source: Australian Research Council
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Intramolecular 1,3-dipolar cycloadditions of two N-alkenylnitrones are studied by means of density functional theory calculations. Cycloaddition of an acyclic 4-hexenylnitrone led to the expected isoxazolidine in 46% yield, but a 4-cycloheptenylnitrone did not react. Calculations of the transition states for cycloaddition indicate that although the cycloheptenyl nitrone has a more favorable activation entropy, the strain associated with distortion of the tethering groups into the required boat conformation disfavors the reaction of the cyclic substrate over the acyclic substrate by 8.7 kcal/mol. (C) 2010 Elsevier Ltd. All rights reserved.
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