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Preparation of 1,3,5-cycloheptatriene and its homologs by the liquid-phase dehydrobromination of 7,7-dibromonorcaranes

✍ Scribed by O. M. Nefedov; É. S. Agavelyan


Book ID
112423437
Publisher
Springer
Year
1972
Tongue
English
Weight
199 KB
Volume
21
Category
Article
ISSN
1573-9171

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Intramolecular cyclopropanation of 7-dia
✍ Henry H. Gu; Keith F. McDaniel; Mark C. McMills; Glenn P.A. Yap; Arnold L. Rhein 📂 Article 📅 1997 🏛 Elsevier Science 🌐 French ⚖ 218 KB

The rhodium(II)-catalyzed diazo decomposition of 7-diazocarbonyltethered-l,3,5-cycloheptatriene 3 generated tricyclic ketoester 4 in 64% yield. Reaction of ketoester 4 with nucleophiles leads to cyclopropane cleavage (Nu --PhSNa) to give 5 or rearrangement (Nu = RNH2) to give 7 or 8.