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

O'Shea, KE, Foote, CS. (1988). Chemistry of Singlet Oxygen. 51. Zwitterionic Intermediates from 2, 4-Hexadienes . JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 110(21), 7167-7170. 10.1021/ja00229a035

cited authors

  • O'Shea, KE; Foote, CS

authors

abstract

  • 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 ~25%, E, E <10%). These observations are explained by intermediate zwitterions that revert to isomerized dienes in competition with collapse to products or capture by methanol. © 1988, American Chemical Society. All rights reserved.

publication date

  • January 1, 1988

published in

Digital Object Identifier (DOI)

start page

  • 7167

end page

  • 7170

volume

  • 110

issue

  • 21