Bicyclic endoperoxides with strained and perturbed diene moiety have been submitted to CoTPP-catalyzed rearrangement. Side reaction, like formation of epoxyenone, has been suppressed and yield of the formation of bisepoxides highly increased.
CoTPP-catalyzed reaction of saturated bicyclic endoperoxides
β Scribed by Metin Balci; Nihat Akbulut
- Book ID
- 108374414
- Publisher
- Elsevier Science
- Year
- 1985
- Tongue
- French
- Weight
- 464 KB
- Volume
- 41
- Category
- Article
- ISSN
- 0040-4020
No coin nor oath required. For personal study only.
π SIMILAR VOLUMES
CoTPP-catalyzed reaction mechanism of the cycloheptatriene 1.4-endoperoxide is studied. Beside the expected bisepoxide, two isomerit open-chain aldehydes are isolated. The mechanism for the formation of the aldehydes are discussed in terms of radical intermediates.
Thermal, and especially photochemical, rearrangement of the endoperoxides (1) and ( )-( ) gives By-epoxycycloalkanones as primary products, accompanied by the expected syn-diepoxides. Unsaturated endoperoxides [e.g.(l)] are readily available by reaction of singlet oxygen ('0,) with conjugated diene