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  Mechanism of the Pummerer Reaction: A Computational Study

Patil, M., Loerbroks, C., & Thiel, W. (2013). Mechanism of the Pummerer Reaction: A Computational Study. Organic Letters, 15(7), 1682-1685. doi:10.1021/ol400468z.

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Item Permalink: https://hdl.handle.net/11858/00-001M-0000-0014-A374-B Version Permalink: https://hdl.handle.net/11858/00-001M-0000-0014-A375-9
Genre: Journal Article

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ol400468z_si_001.pdf (Supplementary material), 2MB
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 Creators:
Patil, Mahendra1, Author           
Loerbroks, Claudia1, Author           
Thiel, Walter1, Author           
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1Research Department Thiel, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445590              

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 Abstract: DFT calculations are used to investigate the mechanism of the Pummerer reaction between a chiral sulfoxide and acetic anhydride under classical and stereoselective reaction conditions (without and with additives, respectively). The first step involving acetylation of the sulfoxide with release of acetate is found to be rate-determining in both cases. For the stereoselective Pummerer reaction in the presence of trimethylsilyl triflate (TMSOTf) and N,N-dimethylacetamide (DMAC), TMSOTf- and DMAC-assisted transition states as well as ion exchange reactions are considered to account for the role of TMSOTf and DMAC.

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Language(s): eng - English
 Dates: 2013-02-202013-03-222013-04-05
 Publication Status: Issued
 Pages: 4
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1021/ol400468z
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Title: Organic Letters
  Abbreviation : Org. Lett.
Source Genre: Journal
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Publ. Info: Washington, DC : American Chemical Society
Pages: 4 Volume / Issue: 15 (7) Sequence Number: - Start / End Page: 1682 - 1685 Identifier: ISSN: 1523-7060
CoNE: https://pure.mpg.de/cone/journals/resource/954925626338