Synthesis of 1,3-bis(silyl/germyl)propanes by hydrosilylation of allylgermanes in the presence of Karstedt catalyst

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Resumo

The hydrosilylation reactions of allylgermanes R3GeAll (R = Cl, Me) in the presence of Karstedt catalyst with a number of phenyl- and thienyl-containing hydridosilanes were studied. It was found that the efficiency of the studied reactions is determined by a combination of several factors: the nature of the substituents at the germanium atoms in the initial olefins; the degree of hydridity of the hydrogen atoms in the initial hydridosilanes; the electronic and steric properties of the substituents at the silicon atoms of the hydridosilanes and their tendency to redistribution of deputies at silicon and germanium atoms. The synthesized compounds were identified using NMR 1H and 13C spectroscopy.

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Sobre autores

V. Lakhtin

State Research Institute of Chemistry and Technology of Organoelement Compounds

Autor responsável pela correspondência
Email: vlachtin@rambler.ru
Rússia, Moscow, 105118

D. Efimenko

State Research Institute of Chemistry and Technology of Organoelement Compounds

Email: vlachtin@rambler.ru
Rússia, Moscow, 105118

A. Shestakova

State Research Institute of Chemistry and Technology of Organoelement Compounds

Email: vlachtin@rambler.ru
Rússia, Moscow, 105118

I. Sokolskaya

State Research Institute of Chemistry and Technology of Organoelement Compounds

Email: vlachtin@rambler.ru
Rússia, Moscow, 105118

N. Kirilina

State Research Institute of Chemistry and Technology of Organoelement Compounds

Email: vlachtin@rambler.ru
Rússia, Moscow, 105118

P. Storozhenko

State Research Institute of Chemistry and Technology of Organoelement Compounds

Email: vlachtin@rambler.ru
Rússia, Moscow, 105118

Bibliografia

  1. Лахтин В.Г., Ефименко Д.А., Филиппов А.М., Шулятьева Т.И., Сокольская И.Б., Семяшкина И.А., Комаленкова Н.Г., Стороженко П.А. // ЖОХ. 2021. Т. 91. Вып. 1. С. 102. doi: 10.31857/S0044460X21010108 ; Lakhtin V.G., Efimenko D.A., Filippov A.M., Shulyatieva T.I., Sokolskaya I.B., Semyashkina I.A., Komalenkova N.G., Storozhenko P.A. // Russ. J. Gen. Chem. 2021. Vol. 91. N 1. P. 77. doi: 10.1134/S1070363221010084
  2. Лахтин В.Г., Ефименко Д.А., Филиппов А.М., Сокольская И.Б., Шестакова А.К., Шулятьева Т.И., Комаленкова Н.Г., Стороженко П.А. // ЖОХ. 2022. Т. 92. Вып. 5. С. 746. doi: 10.31857/S0044460X22050109 ; Lakhtin V.G., Efimenko D.A., Filippov A.M., Sokol’skaya I.B., Shestakova A.K., Shulyatieva T.I., Komalenkova N.G., Storozhenko P.A. // Russ. J. Gen. Chem. 2022. Vol. 92. N 5. P. 811. doi: 10.1134/S1070363222050103
  3. Лахтин В.Г., Ефименко Д.А., Шестакова А.К., Филиппов А.М., Сокольская И.Б., Кирилина Н.И., Стороженко П.А. // ЖОХ. 2023. Т. 93. Вып. 4. С. 548. doi: 10.31857/S0044460X23040078 ; Lakhtin V.G., Efimenko D.A., Shestakova A.K., Filippov A.M., Sokol’skaya I.B., Kirilina N.I., Storozhenko P.A. // Russ. J. Gen. Chem. 2023. Vol. 93. N 4. Р. 815. doi: 10.1134/s1070363223040072
  4. Кобраков К.И., Чернышева Т.И., Карташева Л.И., Наметкин Н.С. // Докл. АН СССР. 1972. Т. 202. № 2. С. 343.
  5. Gilman H.G., Miles D.H. // J. Org. Chem. 1958. Vol. 23. P. 326. doi: 10.1021/jo01096a626
  6. Pitt C.G., Skillern K.R. // J. Organometal. Chem. 1967. Vol. 7. P. 525. doi: 10.1016/S0022-328X(00)85377-2
  7. Beck K.R., Benkeser R.A. // J. Organometal. Chem. 1970. Vol. 21. P. 35. doi: 10.1016/S0022-328X(00)83607-4
  8. Lewis R.N. // J. Am. Chem. Soc. 1947. Vol. 69. P. 717. doi: 10.1021/ja01195a601
  9. Lukevics E., Skorova A.E., Pudova O.A. // Sulfur Rep. 1982. Vol. 2. P. 177. doi: 10.1080/01961778208082436
  10. Schäfer A., Reiβmann M., Jung S., Schäfer A., Saak W., Brendler E., Müller T. // Organometallics. 2013. Vol. 32. P. 4713. doi: 10.1021/om400366z
  11. Herbert S., Rock G. Pat. 3068241 (1948). US // C. A. 1963. Vol. 58. P. 10239.
  12. Benkeser R.A., Foster D.J. // J. Am. Chem. Soc. 1952. Vol. 74. P. 5314. doi: 10.1021/ja01141a026
  13. Russell G. // J. Org. Chem. 1956. Vol. 21. P. 1190. doi: 10.1021/jo01116a614
  14. Hu S.S., Weber W.P. // J. Org. Chem. 1989. Vol. 369. P. 155. doi: 10.1016/0022-328x(89)88003-9
  15. Aronica L.A., Raffa P., Caporusso A.M., Salvadori P. // J. Org. Chem. 2003. Vol. 68. P. 9292. doi: 10.1021/jo0351062
  16. Карташева Л.И., Наметкин Н.С., Чернышева Т.И. // ЖОХ. 1970. Т. 40. Вып. 6. С. 1262.
  17. Lukevits E., Germane S., Pudova O.A., Erchak N.P. // Pharm. Chem. J. 1979. Vol. 13. P. 1040. doi: 10.1007/BF00772250
  18. Миронов В.Ф., Петров А.Д. // Изв. АН СССР. Сер. хим. 1957. № 3. С. 383; Mironov V.F., Petrov A.D. // Bull. Acad. Sci. USSR. Div. Chem. Sci. 1957. Vol. 6. P. 391. doi: 10.1007/BF01173346
  19. Díez-González S., Blanco L. // J. Organometal. Chem. 2008. Vol. 693. P. 2033. doi: 10.1016/j.jorganchem.2008.03.007
  20. Чернышев Е.А., Савушкина В.И., Анисимова В., Каган Е.Г., Шварц Е.Ю. А. с. 362019 (1972) // Б. И. 1973. № 13.
  21. Наметкин Н.С., Кузьмин О.В., Чернышева Т.И., Савушкина В.И., Анисимова В.З., Чернышев Е.А. // Докл. АН СССР. 1970. Т. 193. № 1. С. 110.
  22. Emeléus H.J., Robinson S.R. // J. Chem. Soc. 1947. P. 1592. doi: 10.1039/jr9470001592
  23. Reynolds H.H., Bigelow L.A., Kraus C.A. // J. Am. Chem. Soc. 1929. Vol. 51. P. 3067. doi: 10.1021/ja01385a026

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