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 | Cycloaddition of “N-Acyliminium Ion Pools” with Carbon–Carbon Multiple Bonds
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| | | 1) Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University |
| (Received March 10, 2005)
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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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| doi:10.1246/bcsj.78.1206 | | JOI JST.JSTAGE/bcsj/78.1206 |
| Copyright (c) 2005 The Chemical Society of Japan |
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