Diels–Alder Reactions Between Hexafluoro-2-Butyne and bis-Furyl Dienes: Kinetic versus Thermodynamic Control Full article
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Chemical Communications
ISSN: 1359-7345 , E-ISSN: 1364-548X |
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Output data | Year: 2018, Volume: 54, Number: 23, Pages: 2850-2853 Pages count : 4 DOI: 10.1039/c7cc09466c | ||||||||
Tags | ACETYLENEDICARBOXYLIC ACID; CYCLOADDITIONS; TANDEM; DOMINO; SYSTEMS; N,N'-DIPYRROLYLMETHANE; MECHANISMS; CASCADE; ROUTE; TOOL | ||||||||
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Abstract:
The tandem [4+2] cycloaddition between hexafluoro-2-butyne and bis-furyl dienes, like difurfuryl ester, at room temperature leads to the kinetically controlled “pincer”-adducts – annulated 4a,8a-bis(trifluoromethyl)hexahydro-1,4:5,8-diepoxynaphthalenes. On the other hand, if these reactions proceed at 140 °C, only the thermodynamically controlled “domino”-adducts – annulated 2,3-bis(trifluoromethyl)hexahydro-1,4:5,8-diepoxynaphthalenes – are formed. Therefore, a very rare and unexpected example of full kinetic and thermodynamic control in the Diels–Alder reaction is reported in this paper.
Cite:
Borisova K.K.
, Nikitina E.V.
, Novikov R.A.
, Khrustalev V.N.
, Dorovatovskii P.V.
, Zubavichus Y.V.
, Kuznetsov M.L.
, Zaytsev V.P.
, Varlamov A.V.
, Zubkov F.I.
Diels–Alder Reactions Between Hexafluoro-2-Butyne and bis-Furyl Dienes: Kinetic versus Thermodynamic Control
Chemical Communications. 2018. V.54. N23. P.2850-2853. DOI: 10.1039/c7cc09466c WOS Scopus РИНЦ ANCAN OpenAlex
Diels–Alder Reactions Between Hexafluoro-2-Butyne and bis-Furyl Dienes: Kinetic versus Thermodynamic Control
Chemical Communications. 2018. V.54. N23. P.2850-2853. DOI: 10.1039/c7cc09466c WOS Scopus РИНЦ ANCAN OpenAlex
Files:
Full text from publisher
Dates:
Submitted: | Dec 9, 2017 |
Accepted: | Jan 24, 2018 |
Published online: | Feb 2, 2018 |
Published print: | Mar 21, 2018 |
Identifiers:
Web of science: | WOS:000428844500005 |
Scopus: | 2-s2.0-85044057322 |
Elibrary: | 35514270 |
Chemical Abstracts: | 2018:229038 |
Chemical Abstracts (print): | 168:346635 |
OpenAlex: | W2785478358 |