Indirect cation pool method. Rapid generation of alkoxycarbenium ion pools from thioacetals

Seiji Suga, Kouichi Matsumoto, Koji Ueoka, Jun Ichi Yoshida

Research output: Contribution to journalArticle

63 Citations (Scopus)

Abstract

A sequential one-pot indirect cation pool method has been developed. The method involves the electrochemical generation and accumulation of ArS(ArSSAr)+ at low temperature (step 1) and the follow-up reaction with a thioacetal to generate an alkoxycarbenium ion pool (step 2), which reacts with various carbon nucleophiles (step 3). Steps 2 and 3 are extremely fast. The electrogenerated ArS(ArSSAr)+ was well-characterized by 1H NMR and CSI-MS. The alkoxycarbenium ion pool generated by the present indirect method exhibited 1H and 13C NMR spectra and thermal stability similar to those of the alkoxycarbenium ion pool generated by the direct electrochemical method.

Original languageEnglish
Pages (from-to)7710-7711
Number of pages2
JournalJournal of the American Chemical Society
Volume128
Issue number24
DOIs
Publication statusPublished - Jun 21 2006
Externally publishedYes

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Cations
Positive ions
Ions
Nuclear magnetic resonance
Nucleophiles
Thermodynamic stability
Carbon
Hot Temperature
Temperature
Proton Magnetic Resonance Spectroscopy

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Indirect cation pool method. Rapid generation of alkoxycarbenium ion pools from thioacetals. / Suga, Seiji; Matsumoto, Kouichi; Ueoka, Koji; Yoshida, Jun Ichi.

In: Journal of the American Chemical Society, Vol. 128, No. 24, 21.06.2006, p. 7710-7711.

Research output: Contribution to journalArticle

Suga, Seiji ; Matsumoto, Kouichi ; Ueoka, Koji ; Yoshida, Jun Ichi. / Indirect cation pool method. Rapid generation of alkoxycarbenium ion pools from thioacetals. In: Journal of the American Chemical Society. 2006 ; Vol. 128, No. 24. pp. 7710-7711.
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