Mechanism of the cyclization of dimethyl diethynyl silane with selenium tetrabromide: Computational and structural studies, and monitoring

  • Amosova S
  • Shagun V
  • Martynov A
 et al. 
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Abstract

The structure of 2,4-dibromo-2-dibromomethyl-3,3-dimethyl-1-selena-3-silacyclopentene-4, formed by regioselective electrophilic addition of SeBr4to dimethyl diethynyl silane, has been determined using X-ray analysis technique. Quantum chemistry methods were used to study elementary stages of the reaction. It was found that the first stage consisted of SeBr4conversion into bimolecular complex Br2⋯SeBr2, initiated by dimethyl diethynyl silane. Possible formation of five-membered and six-membered heterocycles involves different cyclization mechanisms. The formation of only five-membered heterocycle is explained by kinetically preferable ring closure through four-center transition state. The conclusions obtained by calculations were confirmed by monitoring of the reaction using1H NMR method. © 2007 Elsevier B.V. All rights reserved.

Author-supplied keywords

  • Chalcogens
  • Five-membered unsaturated heterocycles
  • NMR spectroscopy
  • Reaction mechanisms
  • X-ray diffraction

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Authors

  • Svetlana V. Amosova

  • Vladimir A. Shagun

  • Alexander V. Martynov

  • Natalia A. Makhaeva

  • Lyudmila I. Larina

  • Konstantin A. Lysenko

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