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Synthesis of α-Glycol Monoallyl Ethers

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Abstract

Allyl chloromethyl and allyl 1-chloroethyl ethers reacted with carbonyl compounds in the presence of fine zinc shavings and a catalytic amount of HgCl2 in a mixture of benzene, ethyl acetate, and HMPA (10:5:1) under nitrogen to give the corresponding α-glycol monoallyl ethers in up to 68.1% yield.

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REFERENCES

  1. Jiang, B., Chen, Z., and Tang, X., Org. Lett., 2002, vol. 4, p. 3451. https://doi.org/10.1021/jo0157324

    Article  CAS  PubMed  Google Scholar 

  2. Trost, B.M. and Üeiss, A.H., Adv. Synth. Catal., 2009, vol. 351, p. 963. https://doi.org/10.1002/adsc.200800776

    Article  CAS  Google Scholar 

  3. Anand, N.K. and Carriera, E.M., J. Am. Chem. Soc., 2001, vol. 123, p. 9687. https://doi.org/10.1021/ja016378u

    Article  CAS  PubMed  Google Scholar 

  4. Takita, R., Fukuta, Y., Tsuiji, R., Ohshima, T., and Shibasaki, M., Org. Lett., 2005, vol. 7, p. 1363. https://doi.org/10.1021/ol050069h

    Article  CAS  PubMed  Google Scholar 

  5. Lee, S.I., Kim, S.M., Kim, S.Y., and Chung, Y.K., Synlett, 2006, vol. 2006, no. 14, p. 2256. https://doi.org/10.1055/s-2006-949629

    Article  CAS  Google Scholar 

  6. Schuler, M., Silva, F., Bobbio, C., Tessier, A., and Gouverneur, V., Angew. Chem., Int. Ed., 2008, vol. 47, p. 7927. https://doi.org/10.1002/anie.200802162

    Article  CAS  Google Scholar 

  7. Talybov, G.M., Russ. J. Org. Chem., 2018, vol. 54, no. 11, p. 1739, https://doi.org/10.1134/S1070428018110210

    Article  CAS  Google Scholar 

  8. Tejedor, D., Méndez-Abt, G., Cotos, L., and García-Tellado, F., Chem. Soc. Rev., 2012, vol. 42, no. 2, p. 458. https://doi.org/10.1039/C2CS35311C

    Article  Google Scholar 

  9. Su, Ch. and Williard, P.G., Org. Lett., 2010, vol. 12, no. 23, p. 5378. https://doi.org/10.1021/ol102029u

    Article  CAS  PubMed  Google Scholar 

  10. Huang, G., Ke, M., Tao, Yu., and Chen, F., J. Org. Chem., 2020, vol. 85, no. 8, p. 5321. https://doi.org/10.1021/acs.joc.0c00004

    Article  CAS  PubMed  Google Scholar 

  11. Asako, S., Ilies, L., and Nakamura, E., J. Am. Chem. Soc., 2013, vol. 135, no. 47, p. 17755. https://doi.org/10.1021/ja4106368

    Article  CAS  Google Scholar 

  12. Wimmer, F.P., Caporaso, L., Cavallo, L., Mecking, S., and Falivene, L., Macromolecules, 2018, vol. 51, no. 12, p. 4525. https://doi.org/10.1021/acs.macromol.8b00783

    Article  CAS  Google Scholar 

  13. Funicello, M., Chiummiento, L., Lupattelli, P., and Tramutola, F., Synth. Commun., 2015, vol. 45, p. 1799. https://doi.org/10.1080/00397911.2015.1049274

    Article  CAS  Google Scholar 

  14. Yoshida, M., Yano, S., and Hara, S., Synthesis, 2017, vol. 49, no. 6, p. 1295. https://doi.org/10.1055/s-0036-1588095

    Article  CAS  Google Scholar 

  15. Silverstein, R.M., Bassler, G.C., and Morrill, T.C., Spectrometric Identification of Organic Compounds, New York: Wiley, 1974, 3rd ed.

  16. Ionin, B.I., Ershov, B.A., and Kol’tsov, A.I., YaMR-spektroskopiya v organicheskoi khimii (NMR Spectroscopy in Organic Chemistry), Leningrad: Khimiya, 1983.

  17. Structure Determination of Organic Compounds: Tables of Spectral Data, Pretsch, E., Bühlmann, P., and Affolter, C., Eds., Berlin: Springer, 2000, 3rd ed.

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This work was supported by ongoing institutional funding. No additional grants to carry out or direct this particular research were obtained.

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  1. Azerbaijan Technical University, AZ1073, Baku, Azerbaijan

    G. M. Talybov

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  1. G. M. Talybov
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Talybov, G.M. Synthesis of α-Glycol Monoallyl Ethers. Russ J Org Chem 60, 750–752 (2024). https://doi.org/10.1134/S1070428024040274

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