A Theoretical Analysis of 2,3 Sigmatropic Shifts in Allylic Sulfilimines and Sulfoximines
Ab initio calculations at the level MP4(SDTQ,full)/6-31G*//MP2(full)/6-31G* + AVZPE(MP2(full)/6-31G*) support the experimental observation that allylic sulfoximines do not undergo 2,3 sigmatropic shifts. This process is hindered by a high kinetic barrier although the reaction is strongly exothermic.
M. A. Harmata et al., "A Theoretical Analysis of 2,3 Sigmatropic Shifts in Allylic Sulfilimines and Sulfoximines," Tetrahedron Letters, vol. 36, no. 50, pp. 9145 - 9148, Elsevier, Dec 1995.
The definitive version is available at https://doi.org/10.1016/0040-4039(95)01959-L
Petroleum Research Fund
National Science Foundation (U.S.)
Keywords and Phrases
Organosulfur Derivative; Sulfoxide; Drug Structure; Molecular Model; Theory
International Standard Serial Number (ISSN)
Article - Journal
© 1995 Elsevier, All rights reserved.
01 Dec 1995
We thank the Donors of the Petroleum Research Fund, administered by the American Chemical Society, and the National Science Foundation (CHE-8912190 and CHE-9220679) for partial support of this work.