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Rearrangements of ethylene oxide derivatives. Stereoselectivity of the prochiral C1 hydrogens in the boron trifluoride catalysed rearrangement of 1,2-epoxyoctane

โœ Scribed by Coxon, JM; Lim, C


Book ID
121309799
Publisher
Commonwealth Scientific and Industrial Research Organisation Publishing
Year
1977
Tongue
English
Weight
346 KB
Volume
30
Category
Article
ISSN
0004-9425

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Diastereotopic selection of C2 hydrogens
โœ J.M. Coxon; D.Q. McDonald ๐Ÿ“‚ Article ๐Ÿ“… 1988 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 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