Abstract
1-Aryl-1-hydroperoxy-2-imidooxyethanes are selectively formed at room temperature from styrenes, N-hydroxyphthalimide, and atmospheric oxygen with the participation of tert-butyl hydroperoxide as a radical initiator.
References
K. A. Dubkov, G. I. Panov, V. N. Parmon, Russ. Chem. Rev., 2017, 86, 510.
M. Shiri, M. A. Zolfigol, H. G. Kruger, Z. Tanbakouchian, Tetrahedron, 2010, 66, 9077.
G. I. Borodkin, V. G. Shubin, Russ. Chem. Rev., 2017, 86, 18.
Yu. V. Guk, M. A. Ilyushin, E. L. Golod, B. V. Gidaspov, Russ. Chem. Rev., 1983, 52, 284.
X.-Q. Hu, J.-R. Chen, W.-J. Xiao, Angew. Chem., Int. Ed., 2017, 56, 1960.
S. Murarka, Adv. Synth. Catal., 2018, 360, 1735.
F. Recupero, C. Punta, Chem. Rev., 2007, 107, 3800.
S. Wertz, A. Studer, Green Chem., 2013, 15, 311.
T. V. Magdesieva, O. A. Levitskiy, Russ. Chem. Rev., 2018, 87, 707.
R. Bag, P. B. De, S. Pradhan, T. Punniyamurthy, Eur. J. Org. Chem., 2017, 5424.
X.-F. Xia, S.-L. Zhu, Z. Gu, H. Wang, W. Li, X. Liu, Y.- M. Liang, J. Org. Chem., 2015, 80, 5572.
X.-F. Xia, S.-L. Zhu, Q.-T. Hu, C. Chen, Tetrahedron, 2016, 72, 8000.
S.-Q. Tang, A.-P. Wang, M. Schmitt, F. Bihel, Tetrahedron Lett., 2018, 1465.
Y. Lv, X. Wang, H. Cui, K. Sun, W. Pu, G. Li, Y. Wu, J. He, X. Ren, RSC Adv., 2016, 6, 74917.
J. Luo, J. Zhang, J. Org. Chem., 2016, 81, 9131.
S. Samanta, C. Ravi, A. Joshi, V. Pappula, S. Adimurthy, Tetrahedron Lett., 2017, 5 8, 721.
Y. Ishii, K. Nakayama, M. Takeno, S. Saka guchi, T. Iwahama, Y. Nishiyama, J. Org. Chem., 1995, 60, 3934.
E. A. Kurganova, V. N. Sapunov, G. N. Koshel, A. S. Frolov, Russ. Chem. Bull., 2016, 65, 2115.
Y. Yoshino, Y. Hayashi, T. Iwahama, S. Sakaguchi, Y. Ishii, J. Org. Chem., 1997, 62, 6810.
R. Bag, D. Sar, T. Punniyamurthy, Org. Bi omol. Chem., 2016, 14, 3246.
D. Yamamoto, M. Soga, H. Ansai, K. Makino, Org. Chem. Front., 2016, 3, 1420.
A. V. Arzumanyan, I. K. Goncharova, R. A. Novikov, S. A. Milenin, K. L. Boldyrev, P. N. Solyev, Y. V. Tkachev, A. D. Volodin, A. F. Smol'yakov, A. A. Korlyukov, A. M. Muzafarov, Green Chem., 2018, 20, 1467.
L. I. Kuznetsova, N. I. Kuznetsova, O. A. Yakovina, V. N. Zudin, B. S. Bal'zhinimaev, Kinet. Catal., 2018, 59, 735.
I. A. Opeida, A. L. Plekhov, O. V. Kushch, A. G. Matvienko, Russ. J. Phys. Chem., 2011, 85, 1119.
I. B. Krylov, S. A. Paveliev, B. N. Shelimov, B. V. Lokshin, I. A. Garbuzova, V. A. Tafeenko, V. V. Chernyshev, A. S. Budnikov, G. I. Nikishin, A. O. Terent'ev, Org. Chem. Front., 2017, 4, 1947.
A. O. Terent'ev, I. B. Krylov, V. P. Timofeev, Z. A. Starikova, V. M. Merkulova, A. I. Ilovaisky, G. I. Nikishin, Adv. Synth. Catal., 2013, 355, 2375.
A. O. Terent'ev, M. M. Platonov, I. B. Krylov, V. V. Chernyshev, G. I. Nikishin, Org. Biomol. Chem., 2008, 6, 4435.
A. O. Terent'ev, I. B. Krylov, D. A. Borisov, G. I. Nikishin, Synthesis, 2007, 2979.
A. O. Terent'ev, A. V. Kutkin, M. M. Platonov, Z. A. Starikova, Yu. N. Ogibin, G. I. Nikishin, Russ. Chem. Bull., 2005, 54, 1214.
V. A. Vil., G. dos, P. Gomes, M. V. Ekimova, K. A. Lyssenko, M. A. Syroeshkin, G. I. Nikishin, I. V. Alabugin, A. O. Terent'ev, J. Org. Chem., 2018, 83, 13427.
Q. Lu, Z. Liu, Y. Luo, G. Zhang, Z. Huang, H. Wang, C. Liu, J. T. Miller, A. Lei, Org. Lett., 2015, 17, 3402.
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1454–1457, July, 2019.
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Krylov, I.B., Budnikov, A.S., Lastovko, A.V. et al. Addition of N-hydroxyphthalimide and atmospheric oxygen to styrenes using tert-butyl hydroperoxide as a radical initiator. Russ Chem Bull 68, 1454–1457 (2019). https://doi.org/10.1007/s11172-019-2577-1
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DOI: https://doi.org/10.1007/s11172-019-2577-1