Abstract
Efficient and selective methods have been developed for the synthesis of previously unknown organyl [3-(trimethylsilyl)prop-2-yn-1-yl] selenides, organyl prop-2-yn-1-yl selenides, and bis[3-(trimethylsilyl) prop-2-yn-1-yl] selenide by reactions of 3-bromo-1-(trimethylsilyl)prop-1-yne with the corresponding organylselenolates and sodium selenide generated from diorganyl diselenides or elemental selenium by the action of sodium tetrahydridoborate.
Similar content being viewed by others
References
Wirth, T., Organoselenium Chemistry: Synthesis and Reactions, Weinheim: Wiley-VCH, 2011.
Perin, G., Lenardão, E.J., Jacob, R.G., and Panatieri, R.B., Chem. Rev., 2009, vol. 109, p. 1277.
Bhabak, K. and Mugesh, G., Acc. Chem. Res., 2010, vol. 43, p. 1408.
Back, T., Can. J. Chem., 2009, vol. 87, p. 1657.
Potapov, V.A., Amosova, S.V., and Kashik, A.S., Tetrahedron Lett., 1989, vol. 30, p.613.
Bagnoly, L., Casini, S., Marini, F., Santi, C., and Testaferri, L., Tetrahedron, 2013, vol. 69, p.481.
Braverman, S., Pechenick-Azizi, T., Gottlieb, H., and Sprecher, M., Synthesis, 2011, p.577.
Braverman, S., Cherkinsky, M., Kalendar, Yu., Jana, R., Sprecher, M., and Goldberg, I., Synthesis, 2014, vol. 46, p.119.
Zeni, G., Formiga, H.B., and Comasseto, J.V., Tetrahedron Lett., 2000, vol. 41, p. 1311.
Bhasin, K.K., Singh, N., Kumar, R., Deepali, D.G., Mehta, S.K., Klapoetke, T.M., and Crawford, M.-J., J. Organomet. Chem., 2004, vol. 689, p. 3327.
Potapov, V.A. and Amosova, S.V., Phosphorus, Sulfur Silicon Relat. Elem., 1993, vol. 79, p.277.
Hirabayashi, K., Shibagaki, K., and Shimizu, T., Phosphorus, Sulfur Silicon Relat. Elem., 2016, vol. 191, p.268.
Reich, H.J., Shah, S.K., Gold, P.M., and Olson, R.E., J. Am. Chem. Soc., 1981, vol. 103, p. 3112.
Bao, W., Zheng, Y., Zhang, Y., and Zhou, J., Tetrahedron Lett., 1996, vol. 37, p. 9333.
Rong, M., Huang, R., You, Y., and Weng, Z., Tetrahedron, 2014, vol. 70, p. 8872.
Ma, S., Hao, X., Meng, X., and Huang, X., J. Org. Chem., 2004, vol. 69, p. 5720.
Ma, S., Hao, X., and Huang, X., Chem. Commun., 2003, p. 1082.
Potapov, V.A., Panov, V.A., Musalov, M.V., Musalova, M.V., and Amosova, S.V., Russ. J. Org. Chem., 2016, vol. 52, p. 1054.
Musalova, M.V., Musalov, M.V., Potapov, V.A., and Amosova, S.V., Russ. J. Org. Chem., 2012, vol. 48, p. 1569.
Author information
Authors and Affiliations
Corresponding author
Additional information
Original Russian Text © M.V. Musalov, M.V. Andreev, S.V. Amosova, L.I. Larina, V.A. Potapov, 2017, published in Zhurnal Organicheskoi Khimii, 2017, Vol. 53, No. 10, pp. 1483–1486.
Rights and permissions
About this article
Cite this article
Musalov, M.V., Andreev, M.V., Amosova, S.V. et al. Synthesis of [3-(trimethylsilyl)prop-2-yn-1-yl] selenides. Russ J Org Chem 53, 1510–1513 (2017). https://doi.org/10.1134/S1070428017100049
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070428017100049