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An Easy and Straightforward Oxidative Rearrangement of 1,2-Dialkoxy-Substituted Olefins.

✍ Scribed by Francisco J. Fananas; Jorge Alonso; Felix Rodriguez; Javier Borge


Publisher
John Wiley and Sons
Year
2007
Weight
27 KB
Volume
38
Category
Article
ISSN
0931-7597

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✦ Synopsis


Abstract

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Diastereotopic selection of C2 hydrogens
✍ J.M. Coxon; D.Q. McDonald πŸ“‚ Article πŸ“… 1988 πŸ› Elsevier Science 🌐 French βš– 165 KB

Rearrangement of styrene oxide with (a) LiC104 and (b) BF3 to give phenylethanal exhibits diastereotopic selection with migration of the hydrogen trans to the phenyl group being favoured 1.4 and 1.14 times respectively. The rate of rotation about the Cl -C2 bond of the intermediate is comparable, bu