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Substitution reactions involving organoaluminum compounds

8. Alkenylation of β,β′-diacetoxysulfides with dialkylalkenylalanes

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

Abstract

The reaction of β,β′-dichloro- and β,β′-diacetoxysulfides with dialkyl-Z-alkenylalanes has been studied; reaction occurs under mild conditions with retention of Z-configuration in the double bond. The reaction represents a stereospecific method for the synthesis of cyclic Z-homoallyl sulfides. The corresponding cycloalkanes and cycloalkenes can be obtained from these Z-homoallylic sulfides by desulfurization with Li in ethylamine or with Raney nickel.

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Authors and Affiliations

  1. Institute of Chemistry, Bashkir Scientific Center, Ural Branch, Academy of Sciences of the USSR, Ufa

    N. I. Andreeva, A. V. Kuchin, L. M. Khalilov & G. A. Tolstikov

Authors
  1. N. I. Andreeva
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  2. A. V. Kuchin
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  3. L. M. Khalilov
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  4. G. A. Tolstikov
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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 8, pp. 1869–1874, August 1989.

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Andreeva, N.I., Kuchin, A.V., Khalilov, L.M. et al. Substitution reactions involving organoaluminum compounds. Russ Chem Bull 38, 1715–1720 (1989). https://doi.org/10.1007/BF00956961

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  • DOI: https://doi.org/10.1007/BF00956961

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