The Use of tert-Butyl Vinyl Ether in Stepwise Electrophilic Addition Reactions |
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| Authors: | Leonid N. Koikov Mingming Han Dawn M. Wellman Jim A. Kelly Irina P. Smoliakova |
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| Affiliation: | 1. Chemistry Department , University of North Dakota , Grand Forks, ND, 58202, USA;2. Chemistry Department , University of North Dakota , Grand Forks, ND, 58202, USA;3. NSF-REU program participants |
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| Abstract: | tert-Butyl vinyl ether (1) reacts with p-TolSCl to give 2-tert-butoxy-2-chloroethyl p-tolyl sulfide (2). In the presence of SnCl4, 2 reacts with silyl enol ethers, allyltrimethylsilane, and vinyl ethers to form a C-C bond. In the case of vinyl ethers, the reaction proceeds through the formation of the 5-membered sulfonium salt intermediate which in turn can react with H2O, TMSCN, allyltrimethylsilane, and Grignard reagents. |
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