Abstract
The reactions of mixed ylides containing a diazonium fragment and an "onium" group of different nature with nucleophiles were studied. In the iodonium-diazonium and sulfoniumdiazonium ylide, the nucleophile first of all substitutes the iodonium and sulfonium group. A series of hetaryl-substituted phosphazines was obtained by a one-pot process of nucleophilic substitution in a diazonium-iodonium ylide with subsequent nucleophilic addition of triarylphosphine at the diazo group.
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References
O. I. Kolodiazhny, Phosphorus Ylides: Chemistry and Application in Organic Synthesis, Wiley, New York, 1999.
B. M. Trost, L. S. Melvin, Sulfur Ylides, Academic Press, New York, 1976.
X. Sun, Y. Tang, Acc. Chem. Res., 2008, 41, 937.
K. Jiang, Y. Chen, Tetrahedron Lett., 2014, 55, 2049.
P. J. Stang, V. V. Zhdankin, Chem. Rev., 1996, 96, 1123.
G. K. Murphy, C. Stewart, F. West, Y. Gfu, H-J. Wang, S. Chong, Q. Guo, L. Liu, J. Org. Chem., 2009, 74, 810.
A. K. Srivastava, A. K. Chaurasia, J. Chem. Sci., 2004, 116, 55.
K. Prajapati, A. Varshney, Int. J. Org. Chem., 2011, 1, 57.
S. Patai, The Chemistry of Diazonium and Diazo Groups, Wiley, New York, 1978.
H. Staudinger, J. Meyer, Helv. Chim. Acta, 1919, 2, 619.
H. Staudinger, J. Meyer, Helv. Chim. Acta, 1919, 2, 635.
M. Regitz, A.E.-R.M. Tawfik, H. Heydt, Liebigs Ann. Chem., 1981, 1865.
R. Weiss, J. Seubert, F. Hampel, Angew. Chem., Int. Ed., 1994, 33, 1952.
D. Bethell, S. Dunn, M. M. Khodaei, A. R. Newall, J. Chem. Soc. Perkin Trans. II, 1989, 1829.
D. Bethell, R. Bourne, M. Kasran, J. Chem. Soc. Perkin Trans. II, 1994, 2081.
V. V. Zhdankin, P. J. Stang, Chem. Rev., 2008, 108, 5299.
M. S. Yusubov, A. Yoshimura, V. V. Zhdankin, ARKIVOC, 2016, 342.
E. D. Matveeva, T. A. Podrugina, Y. K. Grishin, A. S. Pavlova, N. S. Zefirov, Russ. J. Org. Chem., 2007, 43, 201.
E. D. Matveeva, T. A. Podrugina, A. S. Pavlova, A. V. Mironov, N. S. Zefirov, Russ. Chem. Bull., 2008, 57, 400.
E. D. Matveeva, T. A. Podrugina, A. S. Pavlova, A. V. Mironov, N. S. Zefirov, Russ.Chem. Bull., 2008, 57, 2237.
E. D. Matveeva, T. A. Podrugina, M. A. Taranova, E. Yu. Melikhova, R. Gleiter, N. S. Zefirov, Tetrahedron, 2013, 69, 7395.
E. D. Matveeva, T. A. Podrugina, M. A. Taranova, D. S. Vinogradov, R. Gleiter, N. S. Zefirov, J. Org. Chem., 2013, 78, 11691.
E. D. Matveeva, D. S. Vinogradov, T. A. Podrugina, T. D. Nekipelova, A. V. Mironov, R. Gleiter, N. S. Zefirov, Eur. J. Org. Chem., 2015, 7324.
C. Schnaars, M. Hennum, T. Bonge-Hansen, J. Org. Chem., 2013, 78, 7488.
S. Muthusamy, P. Srinivasan, Tetrahedron Lett., 2009, 50, 1331.
M. C. Burla, M. Camalli, B. Carrozzini, G. Cascarano, C. Giacovazzo, G. Polidori, R. Spagna, J. Appl. Cryst., 2003, 36, 1103.
V. Petricek, M. Dusek, L. Palatinus, Jana 2000. Structure Determination Software Programs, Institute of Physics, Praha, Czech Republic, 2000.
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Dedicated to the memory of Academician of the Russian Academy of Sciences Nikolai Serafimovich Zefirov (1935–2017), a then team leader who inspired this work.
Organisch-Chemisches Institut der Universität Heidelberg im Neuenheimer Feld, 270 D-69120 Heidelberg, Germany.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 0284–0292, February, 2019.
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Podrugina, T.A., Pavlova, A.S., Vinogradov, D.S. et al. Mixed iodonium-, phosphonium-, arsonium-, sulfoniumdiazonium ylides in reactions with nucleophiles. Russ Chem Bull 68, 284–292 (2019). https://doi.org/10.1007/s11172-019-2384-8
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DOI: https://doi.org/10.1007/s11172-019-2384-8