Photochemical pinacol rearrangements of unsymmetrical diols

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DOIResolve DOI: http://doi.org/10.1021/jo035439z
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TypeArticle
Journal titleJournal Of Organic Chemistry
ISSN00223263
Volume69
Issue6
Pages20172023; # of pages: 7
AbstractThe photochemical pinacol reaction of a series of nonsymmetrical 9-fluorenyl-substituted vic-diols was investigated and compared with their acid-catalyzed thermal reaction. Unlike the thermal reaction, the radiation-induced processes involve only fluorenyl cations, as is reflected in differences of product distribution between the two reactions. From the product studies, substituent migratory aptitudes are reversed in the photochemical process, suggesting that kinetic control takes place under neutral conditions unlike the acid-catalyzed thermal reactions. The presence of fluorenyl cation intermediates and their lifetimes were established by laser flash spectroscopy studies.
Publication date
AffiliationNational Research Council Canada; NRC Steacie Institute for Molecular Sciences
Peer reviewedNo
Identifier10008226
NPARC number12339222
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Record identifierc5dc4b7d-78ec-463c-b1ac-a07c8641b084
Record created2009-09-11
Record modified2016-05-09
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