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Allylic Oxidation with Selenium Dioxide

CONTROLS
=66 and model <=74) (O18) aromatic;connect (C5 and model <=65) (C7) double;connect (C5 and model >=66 and model <=74) (C7) aromatic;connect (C7 and model >=66 and model <=74) (C12) aromatic;connect (C7 and model >=75) (C12) double;connect (Se16 and model >=66 and model <=74) (C5) partial;connect (C12 and model >=66 and model <=74) (H13) partial;connect (O18 and model >=66 and model <=74) (H13) partial;set labelOffset 0 0;font label 14 arial bold;color label white;select Se16;label Se;frame 1;draw arrow1 ARROW {1.3486843 0.40992832 -0.51851845} {1.9170752 1.2584999 -0.98363113} {-0.8597796 0.30522728 0.29078102};draw arrow2 ARROW {-1.1066618 -0.69078636 0.68679523} {-1.4210072 -0.94995975 1.702364} {0.4013691 -2.0104947 -0.4353943};draw arrow3 ARROW {0.9144287 -1.7674046 -1.0541296} {0.37956238 -0.9883394 -0.5520992} {1.2628269 -0.75541306 -0.8780689};')">

Se allylic oxidation mechanism

Click the structures and reaction arrows in sequence to view the 3D models and animations respectively

The first step is a cycloaddition similar to the carbonyl ene reaction. The allylic seleninic acid produced in the first step undergoes a [2,3]-sigmatropic rearrangement to reinstate the double bond position. Rapid decomposition of the selenium (II) intermediate leads to an allylic alcohol. Oxidation can continue to give the 伪,尾-unsaturated carbonyl product (not animated).

A. Nakamura and M. Nakada, Synthesis (Stuttg)., 2013, 45, 1421鈥?451.

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