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Phosphorus, Sulfur, and Silicon and the Related Elements Volume 70, 1992 - Issue 1
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Original Articles

CONFORMATIONAL PREFERENCES AND RESTRICTED RING INVERSION IN THIANTHRENIUM YLIDES

A. L. Ternay Jr. Department of Chemistry, Center for Medicinal Chemistry Research, Box 19065, The University of Texas at Arlington, Arlington, Texas, 76019, U.S.A.
,
J. Baack Department of Chemistry, Center for Medicinal Chemistry Research, Box 19065, The University of Texas at Arlington, Arlington, Texas, 76019, U.S.A.
&
W. W. Lam Department of Chemistry, Center for Medicinal Chemistry Research, Box 19065, The University of Texas at Arlington, Arlington, Texas, 76019, U.S.A.
Pages 19-23 | Received 06 Jun 1991, Accepted 16 Apr 1992, Published online: 26 May 2009
 
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Abstract

Thianthrene reacts with dialkyl diazomalonates to form, depending upon stoichiometry, both mono-and diylides. The monoylide exists perferentially in the pseudo-equatorial geometry but undergoes ring inversion at room temperature. The trans-diylide, unlike trans-thianthrene disulfoxide, does not undergo rapid ring inversion at room temperature. VT NMR indicates a barrier of 19 kcal/mole.

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