The mechanism of allylic oxidation by selenium dioxide
- 1 January 1980
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 15,p. 706-708
- https://doi.org/10.1039/c39800000706
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.Keywords
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