In contrast to epoxidation, germacrene (1) reacts with 1O2 at the exocyclic double bond faster than at the strained endocyclic double bonds, but with (PhO)3-PO3, germacrene is attacked at the most strained double bond and forms an endocyclic allyl alcohol in contrast to the exocyclic isomers formed in the 1O2 reaction.
T. W. Sam and J. K. Sutherland, J. Chem. Soc., Chem. Commun., 1972, 424 DOI: 10.1039/C39720000424
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