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Addition of diaryl- and dialkylarsines to monosubstituted acetylenes

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Conclusions

  1. 1.

    Diphenylarsine was prepared from chlorodiphenylarsine and lithium tetrahydroaluminate, and ethynyldiphenylarsine was prepared from chlorodiphenylarsine and ethynylmagnesium bromide.

  2. 2.

    Diphenylarsine reacts readily with ethynylbenzene, 1-hexyne, 2-propyn-1-ol, ethyl propiolate, and ethynyldiphenylarsine. The respective products were diphenylstyrylarsine, 1-hexenyldiphenylarsine, 3-(diphenylarsino)-2-propen-1-ol, ethyl 3-(diphenylarsino)acrylate, and vinylenebis[diphenylarsine].

  3. 3.

    Reactions of dibutylarsine with dibutylethynylarsine and with tributylethynyltin gave, respectively, vinylenebis[dibutylarsine] and dibutyl[2-(tributylstannyl)vinyl]arsine.

  4. 4.

    According to the IR spectra of the compounds obtained, all the processes described go with formation of mixtures of cis and trans isomers.

  5. 5.

    Bromine adds to vinylenebis[diphenylarsine] at the double carbon-carbon bond.

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Literature cited

  1. 1.

    A. N. Nesmeyanov and A. E. Borisov, Dokl. Akad. Nauk SSSR,174, 96 (1967).

  2. 2.

    A. N. Nesmeyanov, A. E. Borisov, and N. V. Novikova, Izv. Akad. Nauk SSSR, Ser. Khim.,1967, 815.

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    A. N. Nesmeyanov, A. E. Borisov, and Wang Shih-hua, Izv. Akad. Nauk SSSR, Ser. Khim.,1967, 1141.

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    A. N. Nesmeyanov, A. E. Borisov, and N. V. Novikova, Dokl. Akad. Nauk SSSR,172, 1329 (1967).

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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 9, pp. 1973–1976, September, 1969.

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Nesmeyanov, A.N., Borisov, A.E. & Kudryavtseva, L.V. Addition of diaryl- and dialkylarsines to monosubstituted acetylenes. Russ Chem Bull 18, 1825–1827 (1969). https://doi.org/10.1007/BF00905815

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Keywords

  • Acrylate
  • Bromine
  • Trans Isomer
  • Arsine
  • Dibutyl