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dc.contributor.authorVale, João R.
dc.contributor.authorRimpiläinen, Tatu
dc.contributor.authorSievänen, Elina
dc.contributor.authorRissanen, Kari
dc.contributor.authorAfonso, Carlos A. M.
dc.contributor.authorCandeias, Nuno R.
dc.date.accessioned2018-02-23T11:25:41Z
dc.date.available2019-01-15T22:35:21Z
dc.date.issued2018
dc.identifier.citationVale, J. R., Rimpiläinen, T., Sievänen, E., Rissanen, K., Afonso, C. A. M., & Candeias, N. R. (2018). Pot-Economy Autooxidative Condensation of 2-Aryl-2-lithio-1,3-dithianes. <i>Journal of Organic Chemistry</i>, <i>83</i>(4), 1948-1958. <a href="https://doi.org/10.1021/acs.joc.7b02896" target="_blank">https://doi.org/10.1021/acs.joc.7b02896</a>
dc.identifier.otherCONVID_27851812
dc.identifier.otherTUTKAID_76544
dc.identifier.urihttps://jyx.jyu.fi/handle/123456789/57166
dc.description.abstractThe autoxidative condensation of 2-aryl-2-lithio-1,3-dithianes is here reported. Treatment of 2-aryl-1,3-dithianes with n-BuLi in the absence of any electrophile leads to condensation of three molecules of 1,3-dithianes and formation of highly functionalized α-thioether ketones orthothioesters in 51–89% yields upon air exposure. The method was further expanded to benzaldehyde dithioacetals, affording corresponding orthothioesters and α-thioether ketones in 48–97% yields. The experimental results combined with density functional theory studies support a mechanism triggered by the autoxidation of 2-aryl-2-lithio-1,3-dithianes to yield a highly reactive thioester that undergoes condensation with two other molecules of 2-aryl-2-lithio-1,3-dithiane.
dc.language.isoeng
dc.publisherAmerican Chemical Society
dc.relation.ispartofseriesJournal of Organic Chemistry
dc.subject.otherautooxidative condensation
dc.titlePot-Economy Autooxidative Condensation of 2-Aryl-2-lithio-1,3-dithianes
dc.typearticle
dc.identifier.urnURN:NBN:fi:jyu-201802211552
dc.contributor.laitosKemian laitosfi
dc.contributor.laitosDepartment of Chemistryen
dc.contributor.oppiaineOrgaaninen kemiafi
dc.contributor.oppiaineNanoscience Centerfi
dc.contributor.oppiaineOrganic Chemistryen
dc.contributor.oppiaineNanoscience Centeren
dc.type.urihttp://purl.org/eprint/type/JournalArticle
dc.date.updated2018-02-21T16:15:06Z
dc.type.coarhttp://purl.org/coar/resource_type/c_2df8fbb1
dc.description.reviewstatuspeerReviewed
dc.format.pagerange1948-1958
dc.relation.issn0022-3263
dc.relation.numberinseries4
dc.relation.volume83
dc.type.versionacceptedVersion
dc.rights.copyright© 2018 American Chemical Society. This is a final draft version of an article whose final and definitive form has been published by American Chemical Society. Published in this repository with the kind permission of the publisher.
dc.rights.accesslevelopenAccessfi
dc.subject.ysoorganometalliyhdisteet
dc.subject.ysohapettuminen
dc.subject.ysolitium
jyx.subject.urihttp://www.yso.fi/onto/yso/p28123
jyx.subject.urihttp://www.yso.fi/onto/yso/p9119
jyx.subject.urihttp://www.yso.fi/onto/yso/p29475
dc.relation.doi10.1021/acs.joc.7b02896
dc.type.okmA1


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