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Journal articles
Novel π2s+π2a Electrocyclization of Triethylenic-Malonic Acids Exemplified for a One-Pot Synthesis of New γ-Dilactones cis-Fused with a Cyclopentene
Abstract : A new, easy and rapid synthesis of γ-dilactones is cis-fused with a cyclopentenic ring via cyclization of 7-chlorotriethylenic-malonic acids. The key step implicates an intramolecular cyclization to a cyclopentenyl cation, according to an electrocyclic π2s + π2a conrotatory process. This cyclopentenyl cation led to unstable γ-lactones intermediates that are rearrange to more stable isomers. δ-lactones (6Z and 6E-(3-chlorobut-2-en-2-yl)-5-methyl-3,6-dihydro-2H-pyran-2-one) were obtained as secondary products. Mechanistic pathways were considered. The structures of the newly synthesized compounds were established by elemental and spectral data.
Cited literature [7 references]
https://hal.univ-reunion.fr/hal-01188092
Contributor : Claire Tessier <>
Submitted on : Saturday, November 19, 2016 - 8:39:09 AM
Last modification on : Thursday, June 18, 2020 - 3:20:41 AM
Document(s) archivé(s) le : Tuesday, March 21, 2017 - 12:45:49 PM
Contributor : Claire Tessier <>
Submitted on : Saturday, November 19, 2016 - 8:39:09 AM
Last modification on : Thursday, June 18, 2020 - 3:20:41 AM
Document(s) archivé(s) le : Tuesday, March 21, 2017 - 12:45:49 PM
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Dillenschneider2016_hal.pdf
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