Chemistry of Singlet Oxygen. 51. Zwitterionic Intermediates from 2,4-Hexadienes

Article abstract of DOI:10.1021/ja00229a035

The three isomeric 2,4-hexadienes give nearly identical product distributions with singlet oxygen.Singlet oxygen causes rapid interconversion of the isomers, and methoxy hydroperoxides are formed from all three dienes in methanol (E,Z and Z,Z ca. 25 percent, E,E < 10 percent).These observations are explained by intermediate zwitterions that revert to isomerized dienes in competition with collapse to products or capture by methanol.