The Role of Ylides in the Chlorination of Unsymmetrical Sulfides: An Ab Initio Molecular Orbital Study

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Contents Vol 58(2)

doi:10.1071/CH03219

The Role of Ylides in the Chlorination of Unsymmetrical Sulfides: An Ab Initio Molecular Orbital Study

Michael Potvin ^A, Belquis Mothana ^A, Laura Albrecht ^A, Katherine Valenta Darvesh ^A ^C, Richard F. Langler ^B ^D

^A Department of Chemistry, Mount St. Vincent University, Halifax, Nova Scotia B3M 2J6, Canada.
^B Department of Chemistry, Mount Allison University, Sackville, New Brunswick E4L 1G8, Canada.
^C Corresponding author (computations). Email: Katherine.Darvesh@msvu.ca
^D Corresponding author (organic chemistry). Email: rlangler@mta.ca





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Australian Journal of Chemistry 58(2) 143–148 http://dx.doi.org/10.1071/CH03219
Submitted: 27 August 2003 Accepted: 23 September 2004 Published online: 21 February 2005

Abstract

Ab initio molecular orbital theory has been used to investigate a series of possible chlorosulfonium ylides to assess the potential for ylide intermediacy in the chlorination of organic sulfides. The majority of optimized structures are best viewed as thionium salts. Only ylide structures in which the putative carbanionic centre bears a powerful anion stabilizer (e.g. cyano or carbomethoxy) survive optimization.