Abstract
The nucleophilic substitution in mixed phosphonium-iodonium ylides was investigated. The iodonium group is replaced by such S-containing nucleophiles as the thiocyanate anion or thiourea, as well as by halide ions. The structure of the reaction product with the thiocyanate ion was established by X-ray diffraction. A one-pot process involving the nucleophilic substitution and the Wittig reaction was developed.
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E. D. Matveeva, M. V. Proskurnina, N. S. Zefirov, Heteroatom Chem., 2006, 17, 595.
N. Sh. Pirkuliev, V. K. Brel’, N. S. Zefirov, Usp. Khim., 2000, 69, 118 [Russ. Chem. Rev., 2000, 69 (Engl. Transl.)].
P. J. Stang, J. Org. Chem., 2003, 68, 2997.
V. V. Zhdankin, P. J. Stang, Chem. Rev., 2002, 102, 2523.
E. D. Matveeva, T. A. Podrugina, Yu. K. Grishin, V. V. Tkachev, V. V. Zhdankin, S. M. Aldoshin, N. S. Zefirov, Zh. Org. Khim., 2003, 39, 572 [Russ. J. Org. Chem., 2003, 39 (Engl. Transl.)].
E. D. Matveeva, T. A. Podrugina, Yu. K. Grishin, A. S. Pavlova, N. S. Zefirov, Zh. Org. Khim., 2007, 43, 209 [Russ. J. Org. Chem., 2007, 43 (Engl. Transl.)].
V. V. Zhdankin, O. Maydanovych, J. Herschbach, J. Bruno, E. D. Matveeva, N. S. Zefirov, J. Org. Chem., 2003, 68, 1018.
Zh. Huang, X. Yu, X. Huang, J. Org. Chem., 2002, 67, 8261.
J._C. Le Menn, J. Sarrazin, A. Tallec, Can. J. Chem., 1989, 67, 1332.
R. Rossi, F. Bellina, Ch. Bechini, L. Mannina, P. Vergamini, Tetrahedron, 1998, 54, 135.
J. C. J. Bart, J. Chem. Soc. B, 1969, 350.
F. S. Stephens, J. Chem. Soc., 1965, 5640.
A. J. Sreziale, K. W. Ratts, J. Am. Chem. Soc., 1965, 87, 5603.
J. P. Marino, R. J. Linderman, J. Org. Chem., 1983, 48, 4621.
M. C. Burla, M. Camalli, B. Carrozzini, G. Cascarano, C. Giacovazzo, G. Polidori, R. Spagna, J. Appl. Crystallogr., 2003, 36, 1103.
V. Petricek, M. Dusek, L. Palatinus, Jana2000. Structure Determination Software Program, Institute of Physics, Praha (Czech Republic), 2000.
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 391–395, February, 2008.
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Matveeva, E.D., Podrugina, T.A., Pavlova, A.S. et al. One-pot process in phosphonium-iodonium ylides: nucleophilic substitution and the Wittig reaction. Russ Chem Bull 57, 400–405 (2008). https://doi.org/10.1007/s11172-008-0061-4
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DOI: https://doi.org/10.1007/s11172-008-0061-4