Abstract
Methyl 1-bromocyclohexanecarboxylate reacted with zinc and aromatic aldehydes in two steps to afford 16-aryl-15-oxadispiro[5.1.5.3]hexadecane-7,14-diones; methyl 1-[aryl(hydroxy)methyl]cyclohexanecarboxylates were also formed as by-products.
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Shchepin, V.V., Sazhneva, Yu.Kh., and Kirillov, N.F., Sintez i khimicheskie svoistva zameshchennykh 2,3,5,6-tetragidropiran-2,4-dionov (Synthesis and Chemical Properties of Substituted 2,3,5,6-Tetrahydropyran-2,4-diones), Perm: Perm. Univ., 2007, p. 68.
Melekhin, V.S., Kirillov, N.F., Makhmudov, R.R., and Mardanova, L.G., Vestn. Ural. Med. Akad. Nauki, 2009, vol. 25, no. 2, p. 288.
Kirillov, N.F., Makhmudov, R.R., Gavrilov, A.G., Mardanova, L.G., and Vakhrin, M.I., Pharm. Chem. J., 2013, vol. 47, no. 1, p. 40.
Kirillov, N.F. and Shchepin, V.V., Russ. J. Org. Chem., 2001, vol. 37, p. 1223.
Shchepin, V.V., Kirillov, N.F., and Vakhrin, M.I., Russ. J. Gen. Chem., 2004, vol. 74, p. 933.
Shchepin, V.V., Kirillov, N.F., Melekhin, V.S., and Vakhrin, M.I., Russ. J. Gen. Chem., 2006, vol. 76, p. 1421.
Kirillov, N.F. and Melekhin, V.S., Russ. J. Gen. Chem., 2009, vol. 79, p. 1707.
Kirillov, N.F. and Nikiforova, E.A., Russ. J. Org. Chem., 2014, vol. 50, p. 909.
Hussey, A.S. and Newman, M.S., J. Am. Chem. Soc., 1948, vol. 70, p. 3024.
Mineno, M., Sawai, Y., Kanno, K., Sawada, N., and Mizufune, H., J. Org. Chem., 2013, vol. 78, p. 5843.
Unterhalt, B. and Weyrich, K., Arch. Pharm., 1980, vol. 313, p. 795.
CrysAlisPro, Version 1.171.37.33 (release 27-03-2014 CrysAlis171. NET), Agilent Technologies.
Sheldrick, G.M., Acta Crystallogr., Sect. A, 2008, vol. 64, p. 112.
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Original Russian Text © N.F. Kirillov, E.A. Nikiforova, A.N. Vasyanin, M.V. Dmitriev, 2015, published in Zhurnal Organicheskoi Khimii, 2015, Vol. 51, No. 4, pp. 530–534.
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Kirillov, N.F., Nikiforova, E.A., Vasyanin, A.N. et al. Synthesis of 16-aryl-15-oxadispiro[5.1.5.3]hexadecane-7,14-diones by reformatsky reaction. Russ J Org Chem 51, 513–517 (2015). https://doi.org/10.1134/S1070428015040089
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DOI: https://doi.org/10.1134/S1070428015040089