Conclusions
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1.
We have carried out the acetylene condensation of several aromatic iodo compounds in the presence of Cul and K2CO3. We have established the distinctive features of the proposed catalytic scheme.
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2.
The active components of the metallic copper catalyst are Cu (I) compounds.
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3.
Catalytic substitution of aromatic halogen by alkynyl groups involves the intermediacy of copper (I) acetylides.
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4.
We have synthesized 3,5-diethynylpyridine by condensation of 3,5-diiodopyridine with 3-methyl-3-(J-methyl-2-oxabutyloxy)-1-butyne followed by hydrolysis and alkaline cleavage of the diol.
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M. S. Shvartsberg, A. A. Moroz, and I. L. Kotlyarevskii, Izv. Akad. Nauk SSSR, Ser. Khim.,1972, 981.
M. S. Shvartsberg, V. N. Andrievskii, and I. L. Kotlyarevskii, Izv. Akad. Nauk SSSR, Ser. Khim.,3968, 2665.
V. N. Andrievskii, M. S. Shvartsberg, and I. L. Kotlyarevskii, Inventor's Certificate No. 233654 (1968); Byul. Izobr., No. 3, 23 (1969).
M. S. Shvartsberg and A. A. Moroz, Izv. Akad. Nauk SSSR, Ser. Khim.,1971, 1582.
A. N. Kozhevnikova, M. S. Shvartsberg, and I. L. Kotlyarevskii, Izv. Akad. Nauk SSSR, Ser. Khim.,1973, 1168.
M. S. Shvartsberg, A. N. Kozhevnikova, and I. L. Kotlyarevskii, Izv. Akad. Nauk SSSR, Ser. Khim.,1971, 1833.
R. G. R. Bacon and H. A. O. Hill, J. Chem. Soc.,1964, 1097.
C. E. Castro, E. J. Gaughan, and D. C. Owsley, J. Org. Chem.,,31, 4071 (1966).
R. D. Stephens and C. E. Castro, J. Org. Chem.,28, 3313 (1963).
C. E. Castro, R. Havlin, V. K. Honwad, A. Malte, and S. Mojé, J. Am. Chem. Soc.,91, 6464 (1969).
J. Burdon, R. L. Coe, C. R. Marsh, and J. C. Tatlow, J. Chem. Soc., Perkin Trans, 1, 1972, 763.
M. S. Shvartsberg, I. L. Kotlyarevskii, A. N. Kozhevnikova, and V. N. Andrievskii, Izv. Akad. Nauk SSSR, Ser. Khim.,1970, 1144.
M. S. Shvartsberg, A. A. Moroz, and I. L. Kotlyarevskii, Izv. Akad. Nauk SSSR, Ser. Khim.,1971, 1306.
V. V. Korshak, A. M. Sladkov, and Yu. P. Kudryavtsev, Dokl. Akad. Nauk SSSR,144, 115 (1962).
A. A. Moroz and M. S. Shvartsberg, Izv. Akad. Nauk SSSR, Ser. Khim.,1973, 476.
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 4, pp. 875–879, April, 1978.
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Shvartsberg, M.S., Moroz, A.A. & Kozhevnikova, A.N. CU(I) Salts as catalysts of acetylene condensation. Russ Chem Bull 27, 756–760 (1978). https://doi.org/10.1007/BF00925300
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DOI: https://doi.org/10.1007/BF00925300