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

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

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47 Citations (Scopus)


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
Issue number7
Publication statusPublished - Jul 15 2005
Externally publishedYes

ASJC Scopus subject areas

  • Chemistry(all)


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