Journal article
Probing the formation of Bicyclo[4.2.0]octan-1-ols
The Journal of Organic Chemistry, Vol.69(17), pp.5690-5698
2004
Abstract
Reaction of lithium enolates of simple ketones with (±)-phenyl vinyl sulfoxide has potential for the convergent construction of complex fused ring systems containing a bicyclo[n.2.0]alkan-1-ol. The formation of sulfinylbicyclo[4.2.0]octan-1-ols 1−3 from the lithium enolate of cyclohexanone with (±)-phenyl vinyl sulfoxide or (R)-(+)-p-tolyl vinyl sulfoxide 18 was used to probe the mode of this novel cyclization reaction. Using phenyl vinyl sulfoxide, variations in the reaction lighting and solvent were investigated, in conjunction with radical trapping (TEMPO) and isotope labeling (deuterium) experiments. Cyclization to form sulfinylbicyclooctanols 1−3 is likely to proceed via an intermediate that ring closes to the bicycloalkanol anion 11 and was presently favored by the use of solvents such as THF or DME.
Details
- Title
- Probing the formation of Bicyclo[4.2.0]octan-1-ols
- Authors/Creators
- W.A. Loughlin (Author/Creator) - Griffith UniversityC.C. Rowen (Author/Creator) - Griffith UniversityP.C. Healy (Author/Creator) - Griffith University
- Publication Details
- The Journal of Organic Chemistry, Vol.69(17), pp.5690-5698
- Publisher
- ACS Publications
- Identifiers
- 991005543645707891
- Copyright
- © 2004 American Chemical Society
- Murdoch Affiliation
- Murdoch University
- Language
- English
- Resource Type
- Journal article
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