Ring-Opening of Unsymmetrical 1,2-Dioxines Using Cobalt(II) Salen Complexes

Title
Ring-Opening of Unsymmetrical 1,2-Dioxines Using Cobalt(II) Salen Complexes
Publication Date
2005
Author(s)
Greatrex, Ben
( author )
OrcID: https://orcid.org/0000-0002-0356-4966
Email: bgreatre@une.edu.au
UNE Id une-id:bgreatre
Taylor, Dennis K
Type of document
Journal Article
Language
en
Entity Type
Publication
Publisher
American Chemical Society
Place of publication
United States of America
DOI
10.1021/jo040241f
UNE publication id
une:9448
Abstract
The regioselectivity of the metal-catalyzed ring opening of unsymmetrical 1,2-dioxines to cis-y-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.
Link
Citation
The Journal of Organic Chemistry, 70(2), p. 470-476
ISSN
1520-6904
0022-3263
Start page
470
End page
476

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