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Issue 15, 1980
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The mechanism of allylic oxidation by selenium dioxide

Abstract

In the course of the SeO2-oxidation of 5-cyclopentyl-2-methyl[1-13C]pent-2-ene and its isotopomer (2), which stereoselectively yields the E-products (7)–(10), the 13C label is distributed between C-1 and the C-2 substituent, indicating that two separate steps in the sequence determine the stereochemical features of the products; the ene-reaction proceeds in favour of the trans-methyl-group of the olefin by a factor of 7 : 3 and the following [2,3] sigmatropic rearrangement generates the E-configuration of the resulting alcohols.

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Article information


J. Chem. Soc., Chem. Commun., 1980, 706-708
Article type
Paper

The mechanism of allylic oxidation by selenium dioxide

W. Woggon, F. Ruther and H. Egli, J. Chem. Soc., Chem. Commun., 1980, 706
DOI: 10.1039/C39800000706

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