Solvent-Dependent Changes in the Ene Reaction of RTAD with Alkenes:  The Cyclopropyl Group as a Mechanistic Probe

The vinylcyclopropyl moiety was used as an efficient probe to test mechanistic possibilities of the triazolinedione−alkene ene reaction. In non-hydroxylic solvents, this reaction afforded only the ene adducts via a closed three-membered aziridinium imide (AI) intermediate, whereas in hydroxylic solv...

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Bibliographic Details
Published in:Organic letters 2006-01, Vol.8 (1), p.39-42
Main Authors: Roubelakis, Manolis M, Vougioukalakis, Georgios C, Angelis, Yiannis S, Orfanopoulos, Michael
Format: Article
Language:English
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Summary:The vinylcyclopropyl moiety was used as an efficient probe to test mechanistic possibilities of the triazolinedione−alkene ene reaction. In non-hydroxylic solvents, this reaction afforded only the ene adducts via a closed three-membered aziridinium imide (AI) intermediate, whereas in hydroxylic solvents a dipolar intermediate is favored and trapped by the cyclopropyl moiety to form the corresponding cyclopropyl-rearranged solvent-trapped adducts.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol052342l