Butterflyene: an entry into an aesthetically pleasing carbocycle via 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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Bibliographic Details
Published in:Organic & biomolecular chemistry 2023-10, Vol.21 (39), p.7917-7923
Main Authors: Bhatt, Gaurang J., Deota, Pradeep T., Som, Narayan N., Shah, Darshil
Format: Article
Language:English
Subjects:
Diels-Alder reactions
Dienes
Molecular structure
Optimization
Oxidation
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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.
ISSN:1477-0520
1477-0539
DOI:10.1039/d3ob01056b