Issue 23, 2018

Diels–Alder reactions between hexafluoro-2-butyne and bis-furyl dienes: kinetic versus thermodynamic control

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.

Graphical abstract: Diels–Alder reactions between hexafluoro-2-butyne and bis-furyl dienes: kinetic versus thermodynamic control

Supplementary files

Article information

Article type
Communication
Submitted
09 Dec 2017
Accepted
24 Jan 2018
First published
02 Feb 2018
This article is Open Access
Creative Commons BY-NC license

Chem. Commun., 2018,54, 2850-2853

Diels–Alder reactions between hexafluoro-2-butyne and bis-furyl dienes: kinetic versus thermodynamic control

K. K. Borisova, E. V. Nikitina, R. A. Novikov, V. N. Khrustalev, P. V. Dorovatovskii, Y. V. Zubavichus, M. L. Kuznetsov, V. P. Zaytsev, A. V. Varlamov and F. I. Zubkov, Chem. Commun., 2018, 54, 2850 DOI: 10.1039/C7CC09466C

This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. You can use material from this article in other publications, without requesting further permission from the RSC, provided that the correct acknowledgement is given and it is not used for commercial purposes.

To request permission to reproduce material from this article in a commercial publication, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party commercial publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements