Jump to main content
Jump to site search
Access to RSC content Close the message box

Continue to access RSC content when you are not at your institution. Follow our step-by-step guide.


Issue 10, 2013
Previous Article Next Article

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

Back to tab navigation

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

Social activity

Search articles by author

Spotlight

Advertisements