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Prochiral stereoselection of C1 hydrogens in the rearrangement of c1-substituted epoxides: A reexamination of p-methoxystyrene oxide

โœ Scribed by J.M. Coxon; M.P. Hartshorn


Publisher
Elsevier Science
Year
1987
Tongue
French
Weight
165 KB
Volume
28
Category
Article
ISSN
0040-4039

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โœฆ Synopsis


The results of the spontaneous rearrangement of p-methoxystyrene oxide have been reexamined in the light of known stereoselection observed in the rearrangement of Cl-substituted epoxides.


๐Ÿ“œ SIMILAR VOLUMES


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