Butterflyene: an entry into an aesthetically pleasing carbocycle a Diels-Alder reaction on a tetrasubstituted olefin

An interesting molecular architecture, butterflyene, resembling the shape of a butterfly has been synthesized via a sequence of cyclocondensation, benzylic oxidation, McMurry coupling and Diels-Alder reaction (DAR), successively. The DAR of the tetrasubstituted double bond of a bicyclopentylidene mo...

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Published inOrganic & biomolecular chemistry Vol. 21; no. 39; pp. 7917 - 7923
Main Authors Bhatt, Gaurang J, Deota, Pradeep T, Som, Narayan N, Shah, Darshil
Format Journal Article
Published 11.10.2023
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Summary:An interesting molecular architecture, butterflyene, resembling the shape of a butterfly has been synthesized via a sequence of cyclocondensation, benzylic oxidation, McMurry coupling and Diels-Alder reaction (DAR), successively. The DAR of the tetrasubstituted double bond of a bicyclopentylidene moiety with various dienes has been performed to prepare the analogues of butterflyene. DFT calculations have also been used to analyze the structural optimization and reaction energies. An aesthetically pleasing prototype decacyclic ring system resembling the shape of a butterfly has been synthesized in four simple steps. Diels-Alder reactions on a tetrasubstituted double bond give rise to the formation of its analogues.
Bibliography:https://doi.org/10.1039/d3ob01056b
Electronic supplementary information (ESI) available. See DOI
ISSN:1477-0520
1477-0539
DOI:10.1039/d3ob01056b