88078-75-5Relevant academic research and scientific papers
Chemistry of Singlet Oxygen. 51. Zwitterionic Intermediates from 2,4-Hexadienes
O'Shea, Kevin E.,Foote, Christopher S.
, p. 7167 - 7170 (2007/10/02)
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.
-CYCLOADDITION OF SINGLET OXYGEN TO CONJUGATED ACYCLIC HEXADIENES : EVIDENCE OF SINGLET OXYGEN INDUCED cistrans-ISOMERIZATION
Gollnick, Klaus,Griesbeck, Axel
, p. 3303 - 3306 (2007/10/02)
Addition of singlet oxygen to trans,trans-2,4-hexadiene (1) occurs stereospecifically to give endoperoxide 2.With cis,trans-2,4-hexadiene (4), however, a mixture of diastereomeric endoperoxides, 2 + 5, is observed.Evidence of a singlet oxygen - induced cistrans - isomerization is gained by competitive Diels-Alder reaction of 4 with singlet oxygen/diethyl diazenedicarboxylate.
