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Synthesis 2019; 51(16): 3109-3116
DOI: 10.1055/s-0037-1612423
DOI: 10.1055/s-0037-1612423
paper
Synthesis of Diarylacetylenes Bearing Electron-Withdrawing Groups via the Smiles Rearrangement
This work was supported by the Narodowe Centrum Nauki (National Science Centre; grant UNO 2014/15/B/ST5/0218).Further Information
Publication History
Received: 30 January 2019
Accepted after revision: 05 March 2019
Publication Date:
24 April 2019 (online)
Abstract
Nitrobenzyl benzothiazol-2-yl sulfones and nitrobenzyl 1-phenyl-1H-tetrazol-5-yl sulfones react with chlorides of aromatic acids to form β-acyl derivatives. These products undergo the Smiles rearrangement resulting in the formation of the corresponding nitrophenyl arylacetylenes in 50–60% overall yields (approx. 75% per step). Sulfones bearing CF3 or CN groups instead of a NO2 substituent form mixtures of the acetylenes in moderate yields and benzyl aryl ketones in yields above 40%.
Key words
acetylenes - sulfones - Smiles rearrangement - Julia–Kocienski olefination - benzyl ketonesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1612423.
- Supporting Information
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