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 10, 2013

Carbonium vs. carbenium ion-like transition state geometries for carbocation cyclization – how strain associated with bridging affects 5-exo vs. 6-endo selectivity

Author affiliations

Abstract

Quantum chemical calculations are used to explore the origins of regioselectivity for proton-, Pt(II)- and Pd(II)-promoted cyclizations of 1,5-hexadienes, 5-aminoalkenes, and allylic acetimidates. The strain associated with achieving carbonium ion-like transition state geometries is shown to be a key factor in controlling 5-exo vs. 6-endo selectivity.

Graphical abstract: Carbonium vs. carbenium ion-like transition state geometries for carbocation cyclization – how strain associated with bridging affects 5-exo vs. 6-endo selectivity

Supplementary files

Article information


Submitted
13 Jun 2013
Accepted
19 Jul 2013
First published
22 Jul 2013

Chem. Sci., 2013,4, 3894-3898
Article type
Edge Article

Carbonium vs. carbenium ion-like transition state geometries for carbocation cyclization – how strain associated with bridging affects 5-exo vs. 6-endo selectivity

O. Gutierrez, J. G. Harrison, R. J. Felix, F. Cortés Guzman, M. R. Gagné and D. J. Tantillo, Chem. Sci., 2013, 4, 3894 DOI: 10.1039/C3SC51657A

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