Cycloaddition of "N-Acyliminium ion pools" with carbon-carbon multiple bonds

Seiji Suga, Yamato Tsutsui, Aiichiro Nagaki, Jun Ichi Yoshida

Research output: Contribution to journalArticle

45 Citations (Scopus)

Abstract

N-Acyliminium ion pools, which are generated from α-silyl carbamates, were found to react with a variety of alkenes and alkynes to give the corresponding cycloadducts. The reaction with styrene derivatives gave rise to the formation of a significant amount of polymeric products. The use of micromixing, however, resulted in a significant increase in the yield of the cycloadduct at the expense of the polymer. Mechanistic studies indicated that a concerted mechanism seems to be most likely for alkyl-substituted alkenes, whereas a stepwise mechanism seems to be reasonable for aryl-substituted alkenes.

Original languageEnglish
Pages (from-to)1206-1217
Number of pages12
JournalBulletin of the Chemical Society of Japan
Volume78
Issue number7
DOIs
Publication statusPublished - Jul 15 2005
Externally publishedYes

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Cycloaddition
Alkenes
Carbon
Ions
Styrene
Alkynes
Carbamates
Polymers
Derivatives

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Cycloaddition of "N-Acyliminium ion pools" with carbon-carbon multiple bonds. / Suga, Seiji; Tsutsui, Yamato; Nagaki, Aiichiro; Yoshida, Jun Ichi.

In: Bulletin of the Chemical Society of Japan, Vol. 78, No. 7, 15.07.2005, p. 1206-1217.

Research output: Contribution to journalArticle

Suga, Seiji ; Tsutsui, Yamato ; Nagaki, Aiichiro ; Yoshida, Jun Ichi. / Cycloaddition of "N-Acyliminium ion pools" with carbon-carbon multiple bonds. In: Bulletin of the Chemical Society of Japan. 2005 ; Vol. 78, No. 7. pp. 1206-1217.
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