Abstract
A facile method of synthesis of functionally substituted P(IV) derivatives―dialkyl(diaryl)(2-hydroxybenzyl) phosphine oxides―by the reaction of 2-ethoxy-2,3-dihydro[d][1,2]oxaphosphole 2-oxide with organomagnesium compounds, which allows wide variation of substituents on the phosphorus atom was developed.
Article PDF
Similar content being viewed by others
Avoid common mistakes on your manuscript.
References
Litvina, M.N., Chmutova, M.K., Kulyako, Yu.M., and Myasoedov, B.F., Radiochem., 2001, vol. 43, no. 1, p. 66. DOI: 10.1023/A:1012878106998.
Turanov, A.N., Karandashev, V.K., Yarkevich, A.T., Safronova, Z.V., Kharitonov, A.V., Radugina, N.I., and Fedoseyev, A.M., Radiochem., 2004, vol. 46, no. 5, p. 461. DOI: 10.1007/s11137-005-0010-0.
Dogan, O., Bulut, A., Polat, S., and Ali Tecimer, M., Tetrahedron: Asymmetry, 2011, vol. 22, p. 1601. DOI: 10.1016/j.tetasy. 2011.09.003.
Kanai, M., Kato, N., Ichikawa, E., and Shibasaki, M., Synlett, 2005, no. 10, p. 1491. DOI: 10.1055/s-2005-869831.
Morimoto, H., Yoshino, T., Yukawa, T., Lu, G., Matsunaga, S., and Shibasaki M., Angew. Chem. Int. Ed., 2008, vol. 47, p. 9125. DOI: 10.1002/anie.200803682.
Miyata, K., Nakanishi, T., Fushimi, K., and Hasegawa, Y., J. Photochem. Photobiol. A: Chem., 2012, vol. 235, p. 35. DOI: 10.1016/j.jphotochem.2012.03.005.
Mustafina, A., Zairov, R., Gruner, M., Ibragimova, A., Tatarinov, D., Nizameyev, I., Nastapova, N., Yanilkin, V., Kadirov, M., Mironov, V., and Konovalov, A., Colloids Surf. B, 2011, vol. 88, p. 490. DOI: 10.1016/j.colsurfb.2011.07.039.
Xu, H., Yin, K., and Huang, W., J. Phys. Chem. C, 2010, vol. 114, p. 1674. DOI: 10.1021/jp909548t.
Benaglia, M. and Rossi, S., Org. Biomol. Chem., 2010, vol. 8, p. 3824. DOI: 10.1039/c004681g.
Rossi, S., Benaglia, M., Cozzi, F., Genoni, A., and Benincori, T., Adv. Synth. Catal. 2011, vol. 353, p. 848. DOI: 10.1002/adsc.201100122.
Mironov, V.F., Buzykin, B.I., Garayev, R.S., Tatarinov, D.A., Kashapov, L.R., Chestnova, R.V. Nabiullin, V.N., Ilyasov, A.V., and Zobov, V.V., Russ. Chem. Bull., 2014, vol. 63, no. 9, p. 2114. DOI: 10.1007/s11172-014-0708-2.
Safiullina, A.M., Matveeva, A.G., Dvoryanchikova, T.K., Sinegribova, O.A., Tu, A.M., Tatarinov, D.A., and Kostin, A.A., Russ. Chem. Bull., 2012, vol. 61, no. 2, p. 392. DOI: 10.1007/s11172-012-0055-0.
Safiullina, A.M., Matveeva, A.G., Lizunov, A.V., Bodrin, G.V., Goryunov, E.I., Grigoriev, M.S., Semenov, A.A., Brel, V.K., and Nifantiev, E.E., Doklady Chem., 2015, vol. 460, no. 2, p. 57. DOI: 10.1134/S001250081502007X.
Matveeva, A.G., Tu, A.M., Safiulina, A.M., Bodrin, G.V., Goryunov, E.I., Goryunova, I.B., Sinegribova, O.A., and Nifantiev, E.E., Russ. Chem. Bull., 2013, vol. 62, no. 6, p. 1309. DOI: 10.1007/s11172-013-0184-0.
Zairov, R.R., Tatarinov, D.A., Shamsutdinova, N.A., Mustafina, A.R., Rizvanov, I.Kh., Syakaev, V.V., Mironov, V.F., and Konovalov, A.I., Russ. J. Org. Chem., 2014, vol. 50, no. 4, p. 547. DOI: 10.1134/S1070428014040186..
Zairov, R.R., Mustafina, A.R., Shamsutdinova, N., Rummeli, M.H., Amirov, R.R., Burilov, V.A., Pinus, M.V., Morozov, V.I., Ivanov, V.B., Gogolashvili, E.L., Tatarinov, D.A., Mironov, V.F., and Konovalov, A.I., J. Nanopart. Res., 2012, vol. 14, p. 1018. DOI: 10.1007/s11051-012-1018-y.
Engel, R. and Cohen, J.L.I., Synthesis of Carbon–Phosphorus Bonds, Boca Raton: CRC, 2003.
Hartley, F.R., The Chemistry of Organophosphorus Compounds. Phosphine Oxides, Sulphides, Selenides and Tellurides, Chichester: Wiley, 1992, vol.2.
Korbridge, D.E.C., Phosphorus 2000. Chemistry, Biochemistry, and Technology, Amsterdam: Elsevier, 2000.
Tatarinov, D.A., Kostin, A.A., Baranova, T.A., Dobrynin, A.B., Mironova, E.V., Krivolapov, D.B., Buzykin, B.I., and Mironov, V.F., Russ. J. Org. Chem., 2013, vol. 49, no. 4, p. 516. DOI: 10.1134/S1070428013040040.
Tatarinov, D.A., Brel V.K., and Mironov, V.F., Russ. J. Org. Chem. 2015, vol. 51, no. 9, p. 1245. DOI: 10.1134/S1070428015090043.
Mironov, V.F., Tatarinov, D.A., Varaksina, E.N., Baronova, T.A., Zagidullina, I.Ya., Mustafina, A.R., and Konovalov, A.I., RF Patent 2329271, 2008; Byull. Izobret., 2008, no.20.
Tatarinov, D.A., Mironov, V.F., and Varaksina, E.N., Russ. J. Gen. Chem., 2008, vol. 78, no. 6, p. 1287. DOI: 10.1134/S1070363208060340.
Perez-Prieto, J., Galian, R.E., Burgos, P.O., Minana, M.C.M., Miranda, M.A., and Lopez-Ortiz, F., Org. Lett., 2005, vol. 7, no. 18, p. 3869. DOI: 10.1021/ol051254y.
Takagishi, H., Kawakami, K., Kamio, K., and Okuno, K., US Patent 4621123, 1986.
Evreinov, V.I., Baulin, V.E., Vostroknutova, Z.N., Safronova, Z.V., Bondarenko, N.A., and Tsvetkov, E.N., Zh. Obshch. Khim., 1995, vol. 65. no. 2, p.223.
Wang, F., Qu, M., Chen, F., Xu, Q., and Shi, M., Chem. Commun., 2012, vol. 48, p. 8580. DOI: 10.1039/c2cc33908k.
Ivanov, B.E. and Ageeva, A.B., Bull. Acad. Sci. USSR, Div. Chem. Sci., 1967, vol. 16, no. 1, p. 228. DOI: 10.1007/BF00907150.
Author information
Authors and Affiliations
Corresponding author
Additional information
Original Russian Text © D.A. Tatarinov, D.M. Kuznetsov, A.A. Kostin, V.F. Mironov, 2016, published in Zhurnal Obshchei Khimii, 2016, Vol. 86, No. 3, pp. 386–390.
To the 100th Anniversary of A.N. Pudovik
Rights and permissions
About this article
Cite this article
Tatarinov, D.A., Kuznetsov, D.M., Kostin, A.A. et al. 2-Ethoxy-2,3-dihydro[d][1,2]oxaphosphole 2-oxide in the synthesis of dialkyl(diaryl)(2-hydroxybenzyl)phosphine oxides. Russ J Gen Chem 86, 530–533 (2016). https://doi.org/10.1134/S1070363216030063
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070363216030063