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CH⋅⋅⋅O Hydrogen Bonding Influences π-Facial Stereoselective Epoxidations

✍ Scribed by Ilyas Washington; K. N. Houk

Publisher
John Wiley and Sons
Year
2001
Tongue
English
Weight
130 KB
Volume
40
Category
Article
ISSN
0044-8249

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✦ Synopsis

Epoxidations of a-cyclogeranyl systems, such as 1 [Eq. ( )], occur syn to the alkyl group at C3, contrary to expectation based upon steric effects. To determine the origin and scope of this effect, transition structures have been located for oxygen transfer from peracetic acid to several substituted cyclohexenes (2 ± 4) with quantum-mechanical methods. An explanation of the anomalous stereoselectivity of epoxidations of 1 was obtained and predictions were made about the

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Ab initio calcdations at the MP2/6-31G\*//HF/3-21G\* level have been carried out to study Eels-Alder reactions of 2-substituted-1,3-dienes with s u l h dioxide. The CH ... 0 electrostatic interaction detected in some of the transition structures located could be decisive in the control of the exo/en