Diphenylarsine was prepared from chlorodiphenylarsine and lithium tetrahydroaluminate, and ethynyldiphenylarsine was prepared from chlorodiphenylarsine and ethynylmagnesium bromide.
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].
Reactions of dibutylarsine with dibutylethynylarsine and with tributylethynyltin gave, respectively, vinylenebis[dibutylarsine] and dibutyl[2-(tributylstannyl)vinyl]arsine.
According to the IR spectra of the compounds obtained, all the processes described go with formation of mixtures of cis and trans isomers.
Bromine adds to vinylenebis[diphenylarsine] at the double carbon-carbon bond.
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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
- Trans Isomer