Organic & Biomolecular Chemistry
Paper
2-carbonitriles cis-1 were obtained. However, trans-oxirane-2-
carbonitriles trans-1 were obtained with the corresponding
Acknowledgements
aldehydes due to very similar polarities (for details, see the This work was supported by the National Natural Science
ESI†).
Foundation of China (No. 21572017 and 21772010) and the
Fundamental Research Funds for the Central Universities
(XK1802-6).
General procedure for the synthesis of arylacetamides 3
A solution of 3-aryloxirane-2-carbonitrile 1 (0.5 mmol), aniline
(0.55 mmol), and BF3·OEt2 (0.65 mmol) in 5 mL of anhydrous
1,4-dioxane was stirred at 190 °C for 30 min under microwave
irradiation in a sealed vessel. After being cooled to room temp-
erature, the solution system was transferred into a 25 mL flask
and concentrated in vacuo. The residue was purified by flash
column chromatography on silica gel with petroleum ether
and ethyl acetate (8 : 1, v/v) as eluents to afford the corres-
ponding arylacetamides 3.
References
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General procedure for the synthesis of arylacetates 5a–5g
A solution of 3-aryloxirane-2-carbonitrile 1 (0.5 mmol), anhy-
drous alcohol (0.9 mmol) purified with the standard process,
and BF3·OEt2 (0.5 mmol) in 5 mL of anhydrous 1,4-dioxane
was stirred at 175 °C for 30 min under microwave irradiation
in a sealed vessel. After being cooled to room temperature, the
solution system was transferred into a 25 mL flask and concen-
trated in vacuo. The residue was purified by flash column
chromatography on silica gel with petroleum ether and ethyl
acetate (30 : 1, v/v) as eluents to afford the corresponding aryl-
acetates 5a–5g.
General procedure for the synthesis of arylacetic acids 5h–5o
A solution of 3-aryloxirane-2-carbonitrile 1 (0.5 mmol), H2O
(0.6 mmol), and BF3·OEt2 (0.6 mmol) in 5 mL of anhydrous
1,4-dioxane was stirred at 175 °C for 30 min under microwave
irradiation in a sealed vessel. After being cooled to room temp-
erature, the solution system was transferred into a 25 mL flask
and concentrated in vacuo. The residue was purified by flash
column chromatography on silica gel with petroleum ether
and ethyl acetate (10 : 1, v/v) as eluents to afford the corres-
ponding arylacetic acids 5h–5o.
General procedure for the Meinwald rearrangement of
cyanoepoxides 1
A solution of 3-aryloxirane-2-carbonitrile 1 (0.5 mmol) and
BF3·OEt2 (0.65 mmol) or Bi(OTf)3 (0.4 mg, 0.0005 mmol) in
5 mL of anhydrous 1,4-dioxane was stirred at 190 °C for
30 min under microwave irradiation in a sealed vessel. After
being cooled to room temperature, the solution system was
transferred into a 25 mL flask and concentrated in vacuo. The
residue was subjected to GC-MD, NMR, and HRMS analyses,
and further purified by flash column chromatography on silica
gel with petroleum ether and ethyl acetate (8 : 1, v/v) as eluents
to afford a mixture of the corresponding arylacetyl cyanide 6
and arylacetic acid 5.
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Conflicts of interest
There are no conflicts to declare.
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