Russian Journal of General Chemistry

, Volume 89, Issue 7, pp 1545–1548 | Cite as

Synthesis of 1-Naphthylacetylene Sulfides from 4-(1-Naphthyl)-1,2,3-thiadiazole

  • M. Yekhlef
  • M. L. PetrovEmail author
  • L. M. Pevzner
  • E. K. Aleksandrova
Letters to the Editor


4-(1-Naphthyl)-1,2,3-thiadiazole is readily decomposed under the action of potassium tert-butylate with the release of nitrogen and the formation of potassium 2-(1-naphthyl)ethynylthiolate. Upon further treatment of the reaction mixture with excess of alkyl halide, the corresponding alkyl 2-(1-naphthyl)-1-ethynylsulfides have been obtained. In the case of the reaction with allyl bromide, the resulting sulfide has undergone rearrangement. A mixture of Z- and E-isomers of 2-(1-naphthyl)-1-ethynyl-1-propenylsulfide has been obtained as the product of allylic rearrangement instead of the expected product of the thio-Claisen rearrangement.


naphthalene 1,2,3-thiadiazole acetylene sulfides alkylation rearrangement 



This study was financially supported by Ministry of Education and Science of the Russian Federation in the scope of state project no 4.5554.2017/19 using the equipment of the Engineering Center of St. Petersburg State Technological Institute.


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Copyright information

© Pleiades Publishing, Ltd. 2019

Authors and Affiliations

  • M. Yekhlef
    • 1
  • M. L. Petrov
    • 2
    Email author
  • L. M. Pevzner
    • 2
  • E. K. Aleksandrova
    • 2
  1. 1.University of JijelJijelAlgeria
  2. 2.St. Petersburg State Institute of TechnologyTechnical UniversitySt. PetersburgRussia

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