Article
A Theoretical Analysis of 2,3 Sigmatropic Shifts in Allylic Sulfilimines and Sulfoximines
Tetrahedron Letters
Abstract
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.
Department(s)
Chemistry
Sponsor(s)
Petroleum Research FundNational Science Foundation (U.S.)
Comments
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.
Keywords and Phrases
- Organosulfur Derivative,
- Sulfoxide,
- Drug Structure,
- Molecular Model,
- Theory
Document Type
Article - Journal
Document Version
Citation
File Type
text
Language(s)
English
Rights
© 1995 Elsevier, All rights reserved.
Publication Date
12-1-1995
Publication Date
01 Dec 1995
Disciplines
Citation Information
Michael A. Harmata, Rainer Glaser and Grace Shiahuy Chen. "A Theoretical Analysis of 2,3 Sigmatropic Shifts in Allylic Sulfilimines and Sulfoximines" Tetrahedron Letters Vol. 36 Iss. 50 (1995) p. 9145 - 9148 ISSN: 0040-4039 Available at: http://works.bepress.com/rainer-glaser/16/