title: Acid-Promoted Reaction of Trifluoromethylated Allyl Alcohols with Arenes. Stereoselective Synthesis of CF3‑Alkenes and CF3‑Indanes
metadata.name: dc.contributor.author
metadata.value: Kazakova, Anna N.
metadata.lang: -
metadata.name: dc.contributor.author
metadata.value: Iakovenko, Roman O.
metadata.lang: -
metadata.name: dc.contributor.author
metadata.value: Boyarskaya, Irina A.
metadata.lang: -
metadata.name: dc.contributor.author
metadata.value: Nenajdenko, Valentine G.
metadata.lang: -
metadata.name: dc.contributor.author
metadata.value: Vasilyev, Aleksander V.
metadata.lang: -
metadata.name: dc.date.accessioned
metadata.value: 2016-04-10T18:37:24Z
metadata.lang: -
metadata.name: dc.date.available
metadata.value: 2016-04-10T18:37:24Z
metadata.lang: -
metadata.name: dc.date.issued
metadata.value: 2015
metadata.lang: -
metadata.name: dc.identifier.issn
metadata.value: 0022-3263
metadata.lang: -
metadata.name: dc.identifier.uri
metadata.value: http://hdl.handle.net/11701/2038
metadata.lang: -
metadata.name: dc.description.abstract
metadata.value: Reaction of 4-aryl-1,1,1-trifluorobut-3-en-2-ols with arenes under activation with anhydrous FeCl3 or FSO3H was studied. We found that the transformation led to trifluoromethylated alkenes or 1-trifluoromethylated
  indanes (CF3-indanes). The formation of these two types of reaction products strongly depends on the nucleophilicity of the starting arene and the electrophilicity of cationic intermediates generated from CF3-allyl alcohols under reaction conditions. Benzene, anisole, veratrole, and ortho-xylene lead exclusively to CF3-alkenes with an E-configuration. More π-donating polymethylated arenes (pseudocumene, mesitylene) afford only CF3-indanes with a predominantly cis-orientation of substituents at positions 1 and 3 of the indane ring. Meta- and para-xylenes show an intermediate behavior; they may form both CF3-alkenes
  and/or CF3-indanes. The mechanisms of the investigated transformations are discussed.
metadata.lang: en_GB
metadata.name: dc.description.sponsorship
metadata.value: This work was supported by Saint Petersburg State University (grant nos. 12.50.1558.2013 and 12.38.195.2014)
metadata.lang: en_GB
metadata.name: dc.language.iso
metadata.value: en
metadata.lang: en_GB
metadata.name: dc.publisher
metadata.value: ACS Publications
metadata.lang: en_GB
metadata.name: dc.relation.ispartofseries
metadata.value: Journal of Organic Chemistry;80
metadata.lang: -
metadata.name: dc.subject
metadata.value: Trifluoromethylated Allyl Alcohols
metadata.lang: en_GB
metadata.name: dc.subject
metadata.value: arenes
metadata.lang: en_GB
metadata.name: dc.subject
metadata.value: Brønsted or Lewis acids
metadata.lang: en_GB
metadata.name: dc.subject
metadata.value: CF3‑Alkenes
metadata.lang: en_GB
metadata.name: dc.title
metadata.value: Acid-Promoted Reaction of Trifluoromethylated Allyl Alcohols with Arenes. Stereoselective Synthesis of CF3‑Alkenes and CF3‑Indanes
metadata.lang: en_GB
metadata.name: dc.type
metadata.value: Article
metadata.lang: en_GB
resources.filename: untitled.pdf
resources.url: https://dspace.spbu.ru/bitstream/11701/2038/1/untitled.pdf
resources.format: Adobe PDF
resources.size: 1,21 MB