Acetylene-allene-1, 3-diene rearrangement of C4-unsaturated sulfides

Communication 1. Isomeric transformations of 1-tert-butylthiobutadiene-2,3 caused by alkali in alcoholic medium
  • E. N. Prilezhaeva
  • V. N. Petrov
  • G. S. Vasil'ev
  • A. N. Khudyakova
Organic and Biological Chemistry


  1. 1.

    The isomerization of 1-tert-butylthiobutadiene-2,3 by the action of alkali at 130–132° in alcoholic medium leads to the formation of a complex mixture of compounds, containing various aliene, acetylene, and 1,3-diene sulfides. The main isomerization products are 1-tert-butylthiobutadiene-1,3 and 1-tert-butylthiobutyne-1, whose multiple bonds are conjugated with the heteroatom.

  2. 2.

    Under analogous conditions 1-tert-butylthiobutyne-1, 1-tert-butylthiobutyne-2, and also 1-tert-butylthiobutadiene-1, 2 form an equilibrium mixture which does not contain compounds with a 1,3-diene structure. 1-tert-Butylthiobutyne-1 is the main component of this mixture, in which the sulfur atom is conjugated with the C=C bond.

  3. 3.

    The rearrangement mechanism is considered as a prototropic process, proceeding through the formation (by the action of alkali) of intermediate mesomeric anions. Consideration is also given to the role of the heteroatom in this isomerization.



Sulfur Sulfide Acetylene Complex Mixture Sulfur Atom 
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Copyright information

© Consultants Bureau 1970

Authors and Affiliations

  • E. N. Prilezhaeva
    • 1
  • V. N. Petrov
    • 1
  • G. S. Vasil'ev
    • 1
  • A. N. Khudyakova
    • 1
  1. 1.N. D. Zelinskii Institute of Organic ChemistryAcademy of Sciences of the USSRUSSR

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