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Updated: Dec 12, 2025

Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene
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A Mild Method for the Generation and Interception of 1,2-Cycloheptadienes with 1,3-Dipoles
Yaseen A Almehmadi1,2, F G West1
1Department of Chemistry, University of Alberta, W5-70D, Gunning/Lemieux Chemistry Centre, Edmonton, Alberta T6G 2G2, Canada.
Abstract:
1,2-Cycloheptadiene is a strained, transient species that has been underutilized as a synthetic building block. Seven-membered cyclic allenes are mostly known for their propensity to undergo rapid dimerization, and relatively little has been reported regarding their cycloaddition reactivity with 1,3-dienes or 1,3-dipoles. This work describes the trapping of 1-acetoxy-1,2-cycloheptadiene and its unsubstituted counterpart, generated via desilylative elimination, with a range of 1,3-dipolar trapping partners, affording complex polycyclic products with high regio- and diastereoselectivity.
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