The stabilization of thiepin by substitution

B.A. Hess, Jr, L.J. Schaad, David Reinhoudt

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Abstract

Resonance energies of 430 substituted thiepins have been calculated using a simple Hückel method described before. The results predict that thiepins substituted with electron-withdrawing groups (methoxycarbonyl and fluorine) will be less antiaromatic than the parent thiepin. Thus the calculated REPE of the only known type of monocyclic thiepin viz. 3,4 - bis(methoxycarbonyl) - 5 pyrrolidinothiepin (-0.007β) is less negative than that of the parent thiepin.
Original languageUndefined
Pages (from-to)2683-2685
JournalTetrahedron
Volume33
Issue number20
DOIs
Publication statusPublished - 1977

Keywords

  • IR-68372

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