Jump to main content
Jump to site search

Issue 8, 2011
Previous Article Next Article

Photochemical [2 + 2] cycloaddition reactions of 6-alkenyl-3-phenylcyclohex-2-en-1-ones: using biradical conformation control to account for exceptions to the “rule of five”

Author affiliations

Abstract

A series of 6-alkenyl-3-phenylcyclohex-2-enones has been synthesised and the structures of the products obtained from them on irradiation have been determined. The 6-propenyl compounds afforded a tricyclic ‘parallel’ [2 + 2] cycloaddition product and a bicyclic enone resulting from hydrogen abstraction in the biradical intermediate. The 6-butenyl and 6-pentenyl analogues gave ‘crossed’ cycloaddition products only. Although the regiochemistry of these cycloaddition reactions cannot be explained in terms of the ‘rule of five’, it is compatible with the concept of ‘biradical conformation control’ which is based on a consideration of the energy and structure of the possible 1,4-biradical intermediates.

Graphical abstract: Photochemical [2 + 2] cycloaddition reactions of 6-alkenyl-3-phenylcyclohex-2-en-1-ones: using biradical conformation control to account for exceptions to the “rule of five”

Back to tab navigation

Supplementary files

Publication details

The article was received on 07 Dec 2010, accepted on 03 Feb 2011 and first published on 07 Feb 2011


Article type: Paper
DOI: 10.1039/C0OB01131B
Citation: Org. Biomol. Chem., 2011,9, 2959-2968
  •   Request permissions

    Photochemical [2 + 2] cycloaddition reactions of 6-alkenyl-3-phenylcyclohex-2-en-1-ones: using biradical conformation control to account for exceptions to the “rule of five”

    S. A. Bradley, B. J. Bresnan, S. M. Draper, N. W. A. Geraghty, M. Jeffares, T. McCabe, T. B. H. McMurry and J. E. O'Brien, Org. Biomol. Chem., 2011, 9, 2959
    DOI: 10.1039/C0OB01131B

Search articles by author

Spotlight

Advertisements