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http://hdl.handle.net/11701/2038
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Поле DC | Значение | Язык |
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dc.contributor.author | Kazakova, Anna N. | - |
dc.contributor.author | Iakovenko, Roman O. | - |
dc.contributor.author | Boyarskaya, Irina A. | - |
dc.contributor.author | Nenajdenko, Valentine G. | - |
dc.contributor.author | Vasilyev, Aleksander V. | - |
dc.date.accessioned | 2016-04-10T18:37:24Z | - |
dc.date.available | 2016-04-10T18:37:24Z | - |
dc.date.issued | 2015 | - |
dc.identifier.issn | 0022-3263 | - |
dc.identifier.uri | http://hdl.handle.net/11701/2038 | - |
dc.description.abstract | 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. | en_GB |
dc.description.sponsorship | This work was supported by Saint Petersburg State University (grant nos. 12.50.1558.2013 and 12.38.195.2014) | en_GB |
dc.language.iso | en | en_GB |
dc.publisher | ACS Publications | en_GB |
dc.relation.ispartofseries | Journal of Organic Chemistry;80 | - |
dc.subject | Trifluoromethylated Allyl Alcohols | en_GB |
dc.subject | arenes | en_GB |
dc.subject | Brønsted or Lewis acids | en_GB |
dc.subject | CF3‑Alkenes | en_GB |
dc.title | Acid-Promoted Reaction of Trifluoromethylated Allyl Alcohols with Arenes. Stereoselective Synthesis of CF3‑Alkenes and CF3‑Indanes | en_GB |
dc.type | Article | en_GB |
Располагается в коллекциях: | Articles |
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