Bis(acetoxy)iodobenzene → 4-tert-Butylcyclohexanone
Reaktionsgleichung
[C:1]12C[CH:5]([C:6]1(C)C)[CH2:4][CH:3]([C:10]1([CH:20]3CC4CC(C4(C)C)=C3C)[CH2:15]C3CC(C3(C)C)=[C:11]1C)[C:2]=2C.C(OC1C(OC(=O)C)=C(I)C=CC=1)(=[O:33])C>C(Cl)(Cl)(Cl)Cl>[C:10]([CH:3]1[CH2:4][CH2:5][C:6](=[O:33])[CH2:1][CH2:2]1)([CH3:20])([CH3:15])[CH3:11]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a 4-t-butylcyclohexane-1,1-dihydroperoxide and terpinene (trapping reagent) in a stirred room temperature solution of carbon tetrachloride was added, over a period of five to ten minutes, a solution of bisacetoxyiodobenzene (BAIB) in carbon tetrachloride. Rapid bubbling commenced upon addition of the BAIB solution and ceased within a few minutes after addition was completed. Stirring was continued for 0.5 h, after which the solution was filtered through a plug of silica, which was washed with CH2Cl2. The residue obtained upon concentration was purified by column chromatography on silica gel to give 4-t-butyl cyclohexanone and the trapping product ascaridole (endoperoxide of terpinene).