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DOI: 10.1039/A808072K (Paper) Reference Section for: Chem. Commun., 1999, 187-188

Unexpected formation of 3,3a,4,7a-tetrahydrobenzofuran-2,5-diones as well as arene carboxylic acids upon formal double exo nucleophilic addition of R1R2C–COO– to anisolechromium tricarbonyl complexes

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Moncef Bellassoued, Evelyne Chelain, Jérôme Collot, Henri Rudler and Jacqueline Vaissermann

Abstract

Bis(trimethylsily)ketene acetals of the general structure 2 (R1 = H, Me, R2 = Me, Et, Pri, CMe=CH2) react at –78 °C in the presence of ButOK with a series of arenechromium tricarbonyl complexes 3 to give as expected, after oxidation with I2 followed by silica gel chromatography, arylcarboxylic acids 7. In the case of anisolechromium tricarbonyl 8, besides the m-methoxyarylcarboxylic acids, tetrahydrobenzofuran-2,5-diones 11, are formed as the result of a double nucleophilic addition.

References

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  7. Selected data for 4: δH(200 MHz, CDCl3) 7.32–7.27 (m, 3H), 7.05–7.01 (m, 5H), 6.85–6.95 (m, 1H), 4.13 (q, J 8, 2H), 1.55 (s, 6H), 1.17 (t, J 8, 3H). δC(50 MHz, CDCl3) 176.42, 157.12, 147.08, 129.7, 129.55, 123.21, 120.64, 118.7, 111.7, 60.90, 46.50, 26.51, 14.08. MS (EI)m/z 284 (M+). For 6: δH(200 MHz, CDCl) 7.40–7.25 (m, 5H), 4.50–4.25 (m, 2H), 3.60 (dd, J 9.5, 1H), 2.77–2.61 (m, 1H), 2.51–2.35 (m, 1H). δC(50 MHz, CDCl3) 177.6, 136.76, 128.62, 128.0, 127.7, 66.64, 45.57, 31.64. MS (EI)m/z 212 (M+). For 7(R = OPh): δH(200 MHz, CDCl3) 11.0 (br s, 1H), 7.38–6.87 (m, 9H), 3.49 (t, J 6, 1H), 2.10 (m, 1H), 1.77 (m, 1H), 0.92 (t, J 7.2, 3H). δC(50 MHz, CDCl3) 180.43, 157.50, 157.07, 149.43, 129.87, 123.44, 123.87.44, 123.0, 119.01, 118.82, 117.70, 53.30, 26.40, 12.20. MS (EI)m/z 256 (M+). For 11a: mp 69 °C; δH(200 MHz, CDCl3) 6.84 (dd, J 10.2, 3.4, 1H), 6.14 (d, J 10.2, 1H), 5.10 (dd, J 3.4, 0.8, 1H), 2.81 (dd, J 13.8 and 6.4, 1H), 2.51 (ddd, J 13.8, 10.6 and 6.4), 1.25 (s, 3H), 1.09 (s, 3H). δC(50 MHz, CDCl3) 196.17, 180.24, 141.61, 132.12, 70.97, 43.32, 35.25, 24.71, 20.05 .
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