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Please use this identifier to cite or link to this item: http://dspace.bits-pilani.ac.in:8080/jspui/xmlui/handle/123456789/3304
Title: Shifting the Reactivity of Bis-propargyl Ethers from Garratt–Braverman Cyclization Mode to 1,5-H Shift Pathway To Yield 3,4-Disubstituted Furans: A Combined Experimental and Computational Study
Authors: Addy, Partha Sarathi
Keywords: Chemistry
Lipids
Activation energy
Cyclization
Ethers
Issue Date: 16-Dec-2015
Publisher: ACS
Abstract: Aryl or vinyl substituted bis-propargyl ethers upon base treatment generally form phthalans via the Garratt–Braverman (GB) cyclization pathway. In a major departure from this usual route, several aryl/vinyl bis-propargyl ethers with one of the acetylenic arms ending up with 2-tetrahydropyranyloxy methyl or ethoxy methyl have been shown to follow the alternative intramolecular 1,5-H shift pathway upon base treatment. The reaction has led to the formation of synthetically as well as biologically important 3,4-disubstituted furan derivatives in good yields. The initially formed E isomer in solution (CDCl3) slowly isomerizes to the Z isomer, indicating greater stability of the latter. The factors affecting the interplay between the 1,5-H shift and GB rearrangement have also been evaluated, and the results are supported by DFT-based computational study.
URI: https://pubs.acs.org/doi/10.1021/acs.joc.5b02246
http://dspace.bits-pilani.ac.in:8080/xmlui/handle/123456789/3304
Appears in Collections:Department of Chemistry

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