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Issue 9, 2018
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NMR and experimental reinvestigation of the condensation reaction between γ-methylene-α,β-unsaturated aldehydes and propargyl aldehydes

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Abstract

The condensation reaction between a γ-methylene-α,β-unsaturated aldehyde and phenylpropargyl aldehyde was revisited and, guided by extensive DFT calculations of NMR shifts, was found to afford a deconjugative aldol condensation product. In this manner, a simple protocol for the preparation of valuable cross-conjugated oxatrienes was uncovered.

Graphical abstract: NMR and experimental reinvestigation of the condensation reaction between γ-methylene-α,β-unsaturated aldehydes and propargyl aldehydes

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Publication details

The article was received on 15 Dec 2017, accepted on 24 Jan 2018 and first published on 24 Jan 2018


Article type: Communication
DOI: 10.1039/C7OB03110F
Citation: Org. Biomol. Chem., 2018,16, 1442-1447
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    NMR and experimental reinvestigation of the condensation reaction between γ-methylene-α,β-unsaturated aldehydes and propargyl aldehydes

    M. J. Riveira and A. M. Sarotti, Org. Biomol. Chem., 2018, 16, 1442
    DOI: 10.1039/C7OB03110F

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