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 language | English |
|---|---|
| Pages (from-to) | 1206-1217 |
| Number of pages | 12 |
| Journal | Bulletin of the Chemical Society of Japan |
| Volume | 78 |
| Issue number | 7 |
| DOIs | |
| Publication status | Published - Jul 15 2005 |
| Externally published | Yes |
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ASJC Scopus subject areas
- Chemistry(all)
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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 journal › Article
}
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.
UR - http://www.scopus.com/inward/record.url?scp=23244439955&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=23244439955&partnerID=8YFLogxK
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 -