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Germylation and silylation of phenoxy- and phenylthiopropynes and phenoxyallene

  • Organic Chemistry
  • Published:
Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

  1. 1.

    Reaction of triethylgermyllithium with 3-phenoxy- or 3-phenylthio-1-propyne occurs principally in the direction of metallization at the acetylenic hydrogen atom. The isomeric 1-phenoxy- or 1-phenylthio-1-propynes under these conditions do not form addition products at the triple bond. In reaction with phenoxyallene the Et3Ge anion mainly attacks the terminal methylene group.

  2. 2.

    Hydrogermylation and hydrosilylation of these compounds takes place nonregiospecifically with formation of the α and β adducts. Phenoxyallene adds on to triethylgermane in the 1,2- and 2,3- positions.

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Authors and Affiliations

  1. Irkutsk Institute of Organic Chemistry, Siberian Branch of the Academy of Sciences of the USSR, USSR

    G. S. Lyashenko, A. Kh. Filippova, I. D. Kalikhman, V. V. Keiko, O. A. Kruglaya & N. S. Vyazankin

Authors
  1. G. S. Lyashenko
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  2. A. Kh. Filippova
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  3. I. D. Kalikhman
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  4. V. V. Keiko
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  5. O. A. Kruglaya
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  6. N. S. Vyazankin
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 4, pp. 874–878, April, 1981.

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Lyashenko, G.S., Filippova, A.K., Kalikhman, I.D. et al. Germylation and silylation of phenoxy- and phenylthiopropynes and phenoxyallene. Russ Chem Bull 30, 654–658 (1981). https://doi.org/10.1007/BF00949735

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  • DOI: https://doi.org/10.1007/BF00949735

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