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Intramolecular cyclopropanation of 7-diazotethered-1,3,5-cycloheptatriene: Preparation and reactions of tricyclo[5.3.0.02,10]deca-3,5-dien-9-one

✍ Scribed by Henry H. Gu; Keith F. McDaniel; Mark C. McMills; Glenn P.A. Yap; Arnold L. Rheingold

Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
218 KB
Volume
38
Category
Article
ISSN
0040-4039

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✦ Synopsis

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.

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