Home / Publications / The reaction of 1-alkyl-3-phenylpropynones with aromatic aldehydes: an update

The reaction of 1-alkyl-3-phenylpropynones with aromatic aldehydes: an update

Sofia Olegovna Karnakova 1
Sofia Olegovna Karnakova
, 
Dmitrii Andreevich Shabalin 1
Dmitrii Andreevich Shabalin
10.1016/j.mencom.2024.06.037
Published 2024-06-19
Communication , Volume 34, Issue 4, 581-583
3
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Karnakova S. O., Shabalin D. A. The reaction of 1-alkyl-3-phenylpropynones with aromatic aldehydes: an update // Mendeleev Communications. 2024. Vol. 34. No. 4. pp. 581-583.
GOST all authors (up to 50) Copy
Karnakova S. O., Shabalin D. A. The reaction of 1-alkyl-3-phenylpropynones with aromatic aldehydes: an update // Mendeleev Communications. 2024. Vol. 34. No. 4. pp. 581-583.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/j.mencom.2024.06.037
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2024.06.037
TI - The reaction of 1-alkyl-3-phenylpropynones with aromatic aldehydes: an update
T2 - Mendeleev Communications
AU - Karnakova, Sofia Olegovna
AU - Shabalin, Dmitrii Andreevich
PY - 2024
DA - 2024/06/19
PB - Mendeleev Communications
SP - 581-583
IS - 4
VL - 34
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2024_Karnakova,
author = {Sofia Olegovna Karnakova and Dmitrii Andreevich Shabalin},
title = {The reaction of 1-alkyl-3-phenylpropynones with aromatic aldehydes: an update},
journal = {Mendeleev Communications},
year = {2024},
volume = {34},
publisher = {Mendeleev Communications},
month = {Jun},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2024.06.037},
number = {4},
pages = {581--583},
doi = {10.1016/j.mencom.2024.06.037}
}
MLA
Cite this
MLA Copy
Karnakova, Sofia Olegovna, and Dmitrii Andreevich Shabalin. “The reaction of 1-alkyl-3-phenylpropynones with aromatic aldehydes: an update.” Mendeleev Communications, vol. 34, no. 4, Jun. 2024, pp. 581-583. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2024.06.037.

Keywords

acetylenic ketones
aldehydes
alkynones
C–H active compounds
triphenylphosphine.

Abstract

1-Alkyl-3-phenylprop-2-yn-1-ones smoothly react with aromatic aldehydes in the presence of triphenylphosphine (acetonitrile, room temperature, 24 h) to regio- and stereo- selectively afford (Z)-2-benzylideneoxacyclopentan-3-ones in yields up to 93%. The proposed mechanism for the transformation involves 1,3-H proton shift from the alkyl group at the intermediate β-phosphoniovinylide species.

References

.
Conjugated Ynones in Organic Synthesis
Nájera C., Sydnes L.K., Yus M.
Chemical Reviews, 2019
.
Intramolecular hydrogen-bonding-assisted phosphine-catalysed [3 + 2] cyclisation of ynones with o-hydroxy/amino benzaldehydes
Deng Z., Xie Z., Zheng Y., Xiao J., Wang R., Xiang H., Yang H.
Organic and Biomolecular Chemistry, 2019
.
Regio- and stereoselective base-catalyzed assembly of 6-methylene-5-oxaspiro[2.4]heptanones from alkynyl cyclopropyl ketones
Samultceva S.O., Dvorko M.Y., Shabalin D.A., Ushakov I.A., Vashchenko A.V., Schmidt E.Y., Trofimov B.A.
Organic and Biomolecular Chemistry, 2022
.
Phosphine-catalysed denitrative rearomatising (3+2) annulation of α,β-ynones and 3-nitroindoles
Dutta L., Chattopadhyay A., Yadav N., Ramasastry S.S.
Organic and Biomolecular Chemistry, 2023
.
Superbase‐Catalyzed Steric‐Hindrance‐Induced Dimerization of Alkynones to Highly Functionalized Furans
Dvorko M.Y., Shabalin D.A., Ushakov I.A., Schmidt E.Y., Trofimov B.A.
European Journal of Organic Chemistry, 2023