GaCl(3)-catalyzed insertion of diazene derivatives into the cyclopropane ring |
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Authors: | Korotkov Vadim S Larionov Oleg V Hofmeister Anja Magull Jörg de Meijere Armin |
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Affiliation: | Institut für Organische und Biomolekulare Chemie der Georg-August-Universit?t G?ttingen, Tammannstrasse 2, D-37077 G?ttingen, Germany. |
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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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