Abstract
Selenium dibromide selectively brominates lupeol or diacetylbetulin in the presence of NaHCO3 to form an allylic isomer solely. In the absence of soda, the released HBr catalyzes the rearrangement of the allylic isomer into vinylic isomers.
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REFERENCES
Bodrikov, I.V., Kurskii, Yu.A., Chiyanov, A.A., and Subbotin, A.Yu., Russ. J. Org. Chem., 2018, vol. 54, p. 131. https://doi.org/10.1134/S107042801801013X
Potapov, V.A., Kurkutov, E.O., Albanov, A.I., and Amosova, S.V., Russ. J. Org. Chem., 2008, vol. 44, p. 1547. https://doi.org/10.1134/S1070428008100266
Ortgies, S. and Breder, A., ACS Catalysis, 2017, vol. 7, p. 5828. https://doi.org/10.1021/acscatal.7b01216
Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Barone, V., Mennucci, B., Petersson, G.A., Nakatsuji, H., Caricato, M., Li, X., Hratchian, H.P., Izmaylov, A.F., Bloino, J., Zheng, G., Sonnenberg, J.L., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Vreven, T., Montgomery, J.A., Peralta, Jr.J.E., Ogliaro, F., Bearpark, M., Heyd, J.J., Brothers, E., Kudin, K.N., Staroverov, V.N., Kobayashi, R., Normand, J., Raghavachari, K., Rendell, A., Burant, J.C., Iyengar, S.S., Tomasi, J., Cossi, M., Rega, N., Millam, J.M., Klene, M., Knox, J.E., Cross, J.B., Bakken, V., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R.E., Yazyev, O., Austin, A.J., Cammi, R., Pomelli, C., Ochterski, J.W., Marin, R.L., Morokuma, K., Zakrzewski, V.G., Voth, G.A., Salvador, P., Dannenberg, J.J., Dapprich, S., Daniels, A.D., Farkas, Ö., Foresman, J.B., Ortiz, J.V., Cioslowski, J., and Fox, D.J., Gaussian 09, Revision A.1, Gaussian Inc., Wallingford CT, 2009.
Bodrikov, I.V., Kurskii, Yu.A., Chiyanov, A.A., Subbotin, A.Yu., Shavirin, A.S., and Anderson, N.V., J. Sulfur Chem., 2020, vol. 41, p. 280. https://doi.org/10.1080/17415993.2020.1714049
ACKNOWLEDGMENTS
The authors are grateful to A.A. Belikov for help in measuring the NMR spectra. Analyses were performed at the “Analytical Center of the Razuvaev Institute of Organometallic Chemistry of the Russian Academy of Sciences” Center for Collective Use.
Funding
The work was financially supported by the Russian Science Foundation (project no. 19-03-00908).
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Translated from Zhurnal Organicheskoi Khimii, 2022, Vol. 58, No. 8, pp. 906–908 https://doi.org/10.31857/S0514749222080146.
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Bodrikov, I.V., Kurskii, Y.A., Chiyanov, A.A. et al. Selenium Dibromide as a Reagent for Selective Allylic Bromination of Diacetylbetulin and Lupeol. Russ J Org Chem 58, 1178–1179 (2022). https://doi.org/10.1134/S1070428022080140
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DOI: https://doi.org/10.1134/S1070428022080140