Conclusions
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1.
A mixture of the threo- and erythro-isomers of 1,4,4-trideutero-2-perdeutero(methylthiomethyl)-1,2,3-triphenyl-3-butene is formed as the result of reacting perdeuteromethylene-dimethylsulfuran with 1,2,3-triphenylcyclopropene.
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2.
The distribution of the deuterium in the obtained sulfide is in agreement with the scheme of the previously proposed mechanism of the reaction.
Literature cited
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A. Johnson, Chemistry of Ylides [Russian translation], Mir (1969).
R. Breslow and H. W. Chang, J. Am. Chem. Soc.,83, 236 (1965).
W. von Doering and A. K. Hoffmann, J. Am. Chem. Soc.,77, 521 (1955).
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Translated from Izvestlya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 3, pp. 663–665, March, 1977.
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Nesmeyanova, O.A., Kudryavtseva, G.A., Pukitis, G.G. et al. Mechanism for reaction of 1,2,3-triphenylcyclopropene with methylenedimethylsulfuran. Russ Chem Bull 26, 599–601 (1977). https://doi.org/10.1007/BF01179476
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DOI: https://doi.org/10.1007/BF01179476