REVERSIBLE COUPLING OF A SUBSTITUTED ALLYLIC RADICAL WITH MOLECULAR OXYGEN IN A TOCO REACTION OF 5-METHYLHEPTA-1,3,6-TRIENE
p-Toluenethiol/oxygen co-oxidation of 5-methylhepta-1,3,6-triene (1) gives inter alia only one (6a) of four possible diastereoisomeric dioxolanes, and threo- and erythro-isomers of the 1,4-addition product (10, 11).The variation in relative yields with thiol concentration indicates that coupling of the allylic radical (2) with oxygen is reversible.
Barker, Philip J.,Beckwith, Athelstan L. J.,Fung, Y.