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CoTPP-catalyzed reaction mechanism of the cycloheptatriene 1.4-endoperoxide

✍ Scribed by Metin Balci; Yaşar sütbeyaz

Book ID
104221602
Publisher
Elsevier Science
Year
1983
Tongue
French
Weight
181 KB
Volume
24
Category
Article
ISSN
0040-4039

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✦ Synopsis

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.

📜 SIMILAR VOLUMES

CoTPP-catalyzed rearrangement of 1.4-end
CoTPP-catalyzed rearrangement of 1.4-endoperoxides
✍ Metin Balci; Yaşar Sütbeyaz 📂 Article 📅 1983 🏛 Elsevier Science 🌐 French ⚖ 170 KB

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.

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Benzyl chloride and butyl halide each react with CO, catalyzed by 5,10,15,20-tetraphenylporphyrin cobalt (CoTPP) to form phenylacetic acid (in the form of benzyl phenylacetate, the product of electrocarboxylation) or oxalic acid (the direct reduction product of CO,, in the form of dibutyl oxalate),

Acid-Catalyzed Cleavage of 1,4-Dimethyl-
Acid-Catalyzed Cleavage of 1,4-Dimethyl-1,4-dihydronaphthalene 1,4-Endoperoxide. Reactivity of the Resulting Hydroperoxy Carbocation with Nucleophiles
✍ Charles W. Jefford; Jean-Claude Rossier; Shigeo Kohmoto; John Boukouvalas 📂 Article 📅 1985 🏛 John Wiley and Sons 🌐 German ⚖ 653 KB

In the presence of acids, 1,4-dimethyl-l,4-dihydronaphthalene 1,4-endoperoxide readily reacts with nucleophiles to produce methyl-and ring-substituted naphthalenes in high yields. The regioselectivity observed depends on the nucleophile. The key intermediate is shown to be the corresponding hydroper