Journal
GREEN CHEMISTRY
Volume 24, Issue 9, Pages 3805-3813Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d1gc04815e
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Funding
- RUDN University Strategic Academic Leadership Program
- Italian Ministry of Education, University and Research (MIUR) [AIM1829571-1 CUP E61G19000090002]
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This article presents a novel and original protocol for the preparation of complex framework compounds containing a vinylcyclopropane (VCP) fragment. The method involves UV conversion of cyclopentene (CP) derivatives under standard conditions to achieve high yields of target products. Additionally, a one-pot approach for the synthesis of VCPs and the mechanisms of mutual rearrangements of both VCP and CP have been rationalized using DFT calculations.
A novel and original protocol for the preparation of complex framework compounds containing a vinylcyclopropane (VCP) fragment is presented by means of UV conversion of cyclopentene (CP) derivatives under standard conditions, providing high yields of target products in an unprecedented atom economical reversible step. The reverse transformation of compounds with vinylcyclopropyl moieties into CP derivatives takes place in the presence of trifluoroacetic acid at room temperature. A one-pot approach for the synthesis of VCPs from the corresponding benzoazacyclic allenes has also been developed and the mechanisms of mutual rearrangements of both VCP and CP have been rationalized by DFT calculations.
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