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Nitrosoarenes Implement Cascade Cyclization of 1-Allenyl-2-alkynylbenzenes through Diradical Mechanism.

Authors :
Maitra C
Jadhav PD
Barik D
Ho YS
Cheng CC
Cheng MJ
Chiang YW
Liu RS
Source :
Organic letters [Org Lett] 2023 Jan 13; Vol. 25 (1), pp. 82-86. Date of Electronic Publication: 2022 Dec 27.
Publication Year :
2023

Abstract

This work reports cascade cyclization between 1-allenyl-2-alkynylbenzenes and nitrosoarenes. When these two components reacted alone under N <subscript>2</subscript> , N,O-functionalized indane-fused isoxazolidines 3 were obtained selectively. DFT calculations verify that this reaction sequence involves unprecedented nitrone/alkyne cycloadditions, followed by diradical rearrangement.

Details

Language :
English
ISSN :
1523-7052
Volume :
25
Issue :
1
Database :
MEDLINE
Journal :
Organic letters
Publication Type :
Academic Journal
Accession number :
36573784
Full Text :
https://doi.org/10.1021/acs.orglett.2c03884