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Reaction of arylsulfonyl compounds with excess organolithium reagent

Communication 6. Metalation of tert-butyl-3-thienyl sulfone

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Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

  1. 1.

    The reaction of tert-butyl-3-thienyl sulfone with excess n-butyllithium results in the predominant formation of the 2,4-dilithium derivative.

  2. 2.

    tert-Butyl(2,4-dilithium-S-thienyl) sulfone is stable and does not cleave the tert-butylsulfonyl group, in contrast to tert-butyl phenyl sulfone. The difference in the behavior of the sulfones of the benzene and thiophene series is an argument in support of the “arene” mechanism for the cleavage of the tert-butyl-sulfonyl group.

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Author information

Authors and Affiliations

  1. N. D. Zelinskii Institute of Organic Chemistry, Academy of Sciences of the USSR, USSR

    F. M. Stoyanovich, Ya. L. Gol'dfarb & G. B. Chermanova

Authors
  1. F. M. Stoyanovich
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  2. Ya. L. Gol'dfarb
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  3. G. B. Chermanova
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Additional information

See [1] for Communication 5.

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 10, pp. 2285–2290, October, 1973.

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Stoyanovich, F.M., Gol'dfarb, Y.L. & Chermanova, G.B. Reaction of arylsulfonyl compounds with excess organolithium reagent. Russ Chem Bull 22, 2228–2232 (1973). https://doi.org/10.1007/BF01199616

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  • DOI: https://doi.org/10.1007/BF01199616

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