Reactivity of substituted seven-membered heterocyclic sulfones: Spectroelectrochemical study and theoretical modeling

  • Preda L
  • Lazarescu V
  • Hillebrand M
 et al. 
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Abstract

The redox behaviour of four arylidene substituted derivatives of dibenz-[b,e]-thiepin-5,5-dioxide-11-one was investigated in aprotic media by cyclic voltammetry coupled with spectral EPR and UV-vis-absorption techniques. The results point out that the predominant chemical reaction following the electron transfer (ET) is the cleavage of the C-SO2bond (characteristic for the basic heterocycle) and not isomerization and/or coupling reactions (characteristic for the aryl vinyl sulfones). The solvent dependent semiempirical modeling performed in the frame of AMSOL programme package evidences as more probable the cleavage of the C-SO2bond in the phenyl vinyl derivatives 1 and 2 after the second ET, and explains satisfactorily the different behaviour of compounds 3 and 4, determined by the presence of the phenolic OH group. © 2006 Elsevier Ltd. All rights reserved.

Author-supplied keywords

  • C-SO2bond cleavage
  • Heterocyclic sulphones
  • Solvent-dependent PM3 modeling
  • Spectroelectrochemistry

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