A comparative study of Jones's, Collins's and Corey's reagents in the chromium(VI) oxidation of an epimeric pair of allylic alcohols in the benzo-fused Norbornen-5-ol series

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dc.contributor.authorWarrener, R.N.
dc.contributor.authorLee, T.S.
dc.contributor.authorRussell, R.A.
dc.contributor.authorPaddon-Row, M.N.
dc.date.issued1978
dc.description.abstractA comparison has been made between a series of chromium(VI) oxidizing agents, as well as manganese dioxide, a bicyclic allylic secondary alcohol, the exo-ol (7), being the substrate. Jones's, Collins's and Corey's reagents gave, in each case, a mixture of products: the main reactions were epoxidation to yield (8) and (9), normal ketone formation (10), and ring-fragmentation to form the indanol (11) and the indanone (12). All reagents yielded substantial amounts of epoxide, which is rare for Collins's reagent, and unprecedented for Corey's reagent, and varying amounts (13-30 %) of ketone, while Jones's reagent alone gave significant ring-opened products. A dramatic change in product composition was observed with the epimeric endo-alcohol (13), where Jones's reagent (only one studied) yielded the related α,β,-unsaturated ketone (10) in essentially quantitative yield. A discussion of these results is presented in terms of the current understanding of the mechanism of chromium oxidations.
dc.description.statementofresponsibilityRN Warrener, TS Lee, RA Russell and MN Paddon-Row
dc.identifier.citationAustralian Journal of Chemistry: an international journal for chemical science, 1978; 31(5):1113-1127
dc.identifier.doi10.1071/CH9781113
dc.identifier.issn0004-9425
dc.identifier.issn1445-0038
dc.identifier.urihttp://hdl.handle.net/2440/86026
dc.language.isoen
dc.publisherCSIRO Publishing
dc.rights© CSIRO 1978
dc.source.urihttps://doi.org/10.1071/ch9781113
dc.titleA comparative study of Jones's, Collins's and Corey's reagents in the chromium(VI) oxidation of an epimeric pair of allylic alcohols in the benzo-fused Norbornen-5-ol series
dc.typeJournal article
pubs.publication-statusPublished

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