GaCl3-Catalyzed Insertion of Diazene Derivatives into the Cyclopropane Ring1
The Journal of Organic Chemistry2007Vol. 72(20), pp. 7504–7510
Citations Over TimeTop 10% of 2007 papers
Abstract
GaCl3 has been found to efficiently catalyze the formal cycloadditions of diazene derivatives 6 onto 2-arylcyclopropane-1,1-dicarboxylates 5, giving rise to the pyrazolidine derivatives 7. The insertion into the cyclopropane ring proceeds with complete regioselectivity to furnish 5-arylpyrazolidine-1,2,3,3-tetracarboxylates exclusively; however, the cis-configured azo compound N-phenyltriazolinedione gave the two possible regioisomeric pyrazolidine derivatives in ratios varying from 1:1.5 to 1:3. Conceivable mechanisms of these transformations are being discussed.
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