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Reactions of arylsulfonyl compounds with excess organolithium reagent 11. Polar addition to 3-lithioarynes and the synthesis of 2-substituted isophthalic acids

  • Organic Chemistry
  • Published:
Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

  1. 1.

    3-Lichioarynes, generated from t-butyl o,o′-dilithiophenyl sulfones, react by polar addition with lithium aryls, aromatic lithioamides, lithium alkylthiolates, and lithium n-butoxide, by selective addition of the nucleophiles at position 2. Carboxylation of the adducts gives a series of 2-substituted isophthalic acids.

  2. 2.

    The self-condensation of 3-lithioarynes also involves polar addition. We have identified an oligomerization product incorporating three 3-lithioaryne units.

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Authors and Affiliations

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

    F. M. Stoyanovich & M. A. Marakatkina

Authors
  1. F. M. Stoyanovich
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  2. M. A. Marakatkina
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Additional information

Part 10 [1].

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 1, pp. 142–150, January, 1978.

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Stoyanovich, F.M., Marakatkina, M.A. Reactions of arylsulfonyl compounds with excess organolithium reagent 11. Polar addition to 3-lithioarynes and the synthesis of 2-substituted isophthalic acids. Russ Chem Bull 27, 123–129 (1978). https://doi.org/10.1007/BF01153223

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  • DOI: https://doi.org/10.1007/BF01153223

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