Pinacol rearrangement of cyclopent-3-en-1,2-diols: Cyclopentenone formation and interrupting reaction

[Display omitted] •The synthesis of 3,4-dihetarylcyclopent-3-en-1,2-diols is proposed.•The pinacol rearrangement of 3,4-dihetarylcyclopent-3-en-1,2-diols is studied.•Acid-catalysis of cyclopentendiols leads to the formation of cyclopentenyl cation.•The dimerization of cyclopent-3-en-1,2-diols procee...

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Bibliographic Details
Published in:Tetrahedron letters 2018-01, Vol.59 (3), p.243-246
Main Authors: Shirinian, Valerii Z., Lvov, Andrey G., Lonshakov, Dmitry V., Yadykov, Anton V., Kachala, Vadim V., Krayushkin, Mikhail M.
Format: Article
Language:English
Subjects:
Cyclopentenone
Cyclopentenyl cation
Diarylethene
Dimerization
Interrupted reaction
Pinacol rearrangement
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Summary:[Display omitted] •The synthesis of 3,4-dihetarylcyclopent-3-en-1,2-diols is proposed.•The pinacol rearrangement of 3,4-dihetarylcyclopent-3-en-1,2-diols is studied.•Acid-catalysis of cyclopentendiols leads to the formation of cyclopentenyl cation.•The dimerization of cyclopent-3-en-1,2-diols proceeds via self-trapping mechanism. Cyclopentenyl carbocations formed as a result of the protonation of 3,4-substituted cyclopent-3-en-1,2-diols can give either cyclopent-2-en-1-one derivatives via pinacol rearrangement or interrupted reaction products similar to the Nazarov intermediate.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2017.12.016