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Mechanistic Studies on the Base-Promoted Conversion of Alkoxy-Substituted, Ring-Fused gem-Dihalocyclopropanes into Furans: Evidence for a Process Involving Electrocyclic Ring Closure of a Carbonyl Ylide Intermediate

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dc.contributor.authorSharp, Phillip
dc.contributor.authorMikusek, Jiri
dc.contributor.authorHo, Junming
dc.contributor.authorKrenske, Elizabeth
dc.contributor.authorBanwell, Martin
dc.contributor.authorCoote, Michelle
dc.contributor.authorWard, Jas
dc.contributor.authorWillis, Anthony
dc.date.accessioned2020-08-30T23:37:57Z
dc.date.available2020-08-30T23:37:57Z
dc.date.issued2018-10-03
dc.description.abstractThe mechanism associated with the base-promoted conversion of alkoxy-substituted and ring-fused gem-dihalocyclopropanes such as 40 into annulated furans has been explored. Treatment of compound 40 with potassium tert-butoxide affords a mixture of furans 23/27 and 41, an outcome that suggests the intermediacy of the slowly interconverting carbonyl ylides 42 and 43 that undergo rapid [1,5]-electrocyclizations and subsequent dehydrohalogenation to afford the observed products. This proposal is supported by ab initio MO and DFT calculations that also suggest a vinylcarbene insertion pathway is less likely to be operative.en_AU
dc.description.sponsorshipThe authors thank the Australian Research Council and the Institute of Advanced Studies at the Australian National University for financial support.en_AU
dc.format.mimetypeapplication/pdfen_AU
dc.identifier.issn0022-3263en_AU
dc.identifier.urihttp://hdl.handle.net/1885/209116
dc.language.isoen_AUen_AU
dc.provenancehttps://v2.sherpa.ac.uk/id/publication/7797..."The Accepted Version can be archived in a non-commercial institutional repository if required by funder. 12 months embargo." from SHERPA/RoMEO site (as at 28/08/2020)." This document is the Accepted Manuscript version of a Published Work that appeared in final form in The Journal of organic chemistry, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://dx.doi.org/10.1021/acs.joc.8b01766en_AU
dc.publisherAmerican Chemical Societyen_AU
dc.relationhttp://purl.org/au-research/grants/arc/DP170100926
dc.rights© 2018 American Chemical Societyen_AU
dc.sourceThe Journal of organic chemistryen_AU
dc.titleMechanistic Studies on the Base-Promoted Conversion of Alkoxy-Substituted, Ring-Fused gem-Dihalocyclopropanes into Furans: Evidence for a Process Involving Electrocyclic Ring Closure of a Carbonyl Ylide Intermediateen_AU
dc.typeJournal articleen_AU
dcterms.accessRightsOpen Accessen_AU
local.bibliographicCitation.issue22en_AU
local.bibliographicCitation.lastpage13690en_AU
local.bibliographicCitation.startpage13678en_AU
local.contributor.affiliationSharp, P., Research School of Chemistry, The Australian National Universityen_AU
local.contributor.affiliationMikusek, J., Research School of Chemistry, The Australian National Universityen_AU
local.contributor.affiliationHo, Junming, Research School of Chemistry, The Australian National Universityen_AU
local.contributor.affiliationKrenske. E., Research School of Chemistry, The Australian National Universityen_AU
local.contributor.affiliationBanwell, M., Research School of Chemistry, The Australian National Universityen_AU
local.contributor.affiliationCoote, Michelle, Research School of Chemistry, The Australian National Universityen_AU
local.contributor.affiliationWard, J., Research School of Chemistry, The Australian National Universityen_AU
local.contributor.affiliationWillis, A., Research School of Chemistry, The Australian National Universityen_AU
local.contributor.authoruidu851288en_AU
local.identifier.citationvolume83en_AU
local.identifier.doi10.1021/acs.joc.8b01766en_AU
local.identifier.essn1520-6904en_AU
local.publisher.urlhttp://pubs.acs.org/journal/joceah/about.htmlen_AU
local.type.statusAccepted Versionen_AU

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