The stabilization of thiepin by substitution


Hess, Jr, B.A. and Schaad, L.J. and Reinhoudt, D.N. (1977) The stabilization of thiepin by substitution. Tetrahedron, 33 (20). pp. 2683-2685. ISSN 0040-4020

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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.
Item Type:Article
Copyright:© 1977 Elsevier Science
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