Jump to main content
Jump to site search
SCHEDULED MAINTENANCE Close the message box

Maintenance work is planned for Monday 16 August 2021 from 07:00 to 23:59 (BST).

Website performance may be temporarily affected and you may not be able to access some PDFs or images. If this does happen, refreshing your web browser should resolve the issue. We apologise for any inconvenience this might cause and thank you for your patience.


Issue 2, 2014

Distortion-accelerated cycloadditions and strain-release-promoted cycloreversions in the organocatalytic carbonyl-olefin metathesis

Author affiliations

Abstract

The mechanism of hydrazine-catalyzed carbonyl-olefin metathesis relying on a novel (3 + 2) strategy is studied by density functional theory (DFT) calculations. The origins of the special reactivity of cyclopropene in this transformation are revealed, and the reactivities of different alkenes in the (3 + 2) cycloadditions and cycloreversions are compared. It is found that the ease of distortion of reactants accelerates cycloadditions, and that the strain release is the controlling factor for cycloreversions.

Graphical abstract: Distortion-accelerated cycloadditions and strain-release-promoted cycloreversions in the organocatalytic carbonyl-olefin metathesis

Supplementary files

Article information


Submitted
17 Oct 2013
Accepted
01 Nov 2013
First published
04 Nov 2013

Chem. Sci., 2014,5, 471-475
Article type
Edge Article

Distortion-accelerated cycloadditions and strain-release-promoted cycloreversions in the organocatalytic carbonyl-olefin metathesis

X. Hong, Y. Liang, A. K. Griffith, T. H. Lambert and K. N. Houk, Chem. Sci., 2014, 5, 471 DOI: 10.1039/C3SC52882K

To request permission to reproduce material from this article, 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 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

Search articles by author

Spotlight

Advertisements