Ring-opening of unsymmetrical 1,2-dioxines using cobalt (II) salen complexes
Date
2005
Authors
Greatrex, B.
Taylor, D.
Editors
Advisors
Journal Title
Journal ISSN
Volume Title
Type:
Journal article
Citation
Journal of Organic Chemistry, 2005; 70(2):470-476
Statement of Responsibility
Conference Name
Abstract
The regioselectivity of the metal-catalyzed ring opening of unsymmetrical 1,2-dioxines to cis--hydroxyenones was investigated using two different Co(II) salen complexes. Regioselectivity was determined by direct examination of the enone ratios and by derivitization with a stabilized phosphorus ylide. The steric influence of the substituents on the 1,2-dioxine was the primary influence on regioselectivity. Temperature played little role; however, solvent and selection of Co(II) complex could be used to mildly influence the outcome of the rearrangement for selected substrates. The origins of the selectivity for the reaction are discussed.