TY - JOUR
T1 - Cycloaddition of "N-Acyliminium ion pools" with carbon-carbon multiple bonds
AU - Suga, Seiji
AU - Tsutsui, Yamato
AU - Nagaki, Aiichiro
AU - Yoshida, Jun Ichi
PY - 2005/7/15
Y1 - 2005/7/15
N2 - 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.
AB - 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.
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U2 - 10.1246/bcsj.78.1206
DO - 10.1246/bcsj.78.1206
M3 - Article
AN - SCOPUS:23244439955
VL - 78
SP - 1206
EP - 1217
JO - Bulletin of the Chemical Society of Japan
JF - Bulletin of the Chemical Society of Japan
SN - 0009-2673
IS - 7
ER -