Regioselectivity in the Reductive Bond Cleavage of Diarylalkylsulfonium Salts: Variation with Driving Force and Structure of Sulfuranyl Radical Intermediates-Reference-Cited by-同舟云学术

Regioselectivity in the Reductive Bond Cleavage of Diarylalkylsulfonium Salts: Variation with Driving Force and Structure of Sulfuranyl Radical Intermediates

Published:2009-07-06 Issue:29 Volume:131 Page:10015-10022
ISSN:0002-7863
Container-title:Journal of the American Chemical Society
language:en
Short-container-title:J. Am. Chem. Soc.

Author:

Kampmeier Jack A.¹,Hoque AKM Mansurul¹,Saeva Franklin D.¹,Wedegaertner Donald K.¹,Thomsen Pia¹,Ullah Saif¹,Krake Jacob¹,Lund Torben¹

Affiliation:

1. Department of Chemistry, University of Rochester, Rochester, New York 14627, and Department of Science, Systems and Models, Roskilde University, P.O. Box 260, DK-4000 Roskilde, Denmark

Publisher

American Chemical Society (ACS)

Subject

Colloid and Surface Chemistry,Biochemistry,General Chemistry,Catalysis

Link

https://pubs.acs.org/doi/pdf/10.1021/ja809918k

Reference52 articles.

1. STUDIEN ZUM VORGANG DER WASSERSTOFFÜBERTRAGUNG 591SELEKTIVITÄTSSTUDIEN AM BEISPIEL DER REDUKTIVEN SPALTUNG VON METHYL-DIPHENYLSULFONIUMPERCHLORAT

2. One-electron chemical reductions of phenylalkylsulfonium salts

3. Aqueous Phase One-Electron Reduction of Sulfonium, Selenonium and Telluronium Salts

4. For example, the cleavage ratios reported by Hall and Horner(1)are compromised by nucleophilic displacement because they used methylsulfonium salts and tetrabutylammonium bromide as the supporting electrolyte in acetonitrile. As the temperature was increased in their electrolytic experiments, the amount of methyl cleavage increased, as expected for a competing SN2 reaction.

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