The use of tert-Butyl vinyl ether in stepwise electrophllic addition reactions

Article abstract of DOI:10.1080/00397910008086984

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.

Full text of DOI:10.1080/00397910008086984

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Synthetic Communications: An
International Journal for Rapid
Communication of Synthetic
Organic Chemistry
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The Use of tert-Butyl Vinyl
Ether in Stepwise Electrophilic
Addition Reactions
Leonid N. Koikov a , Mingming Han a , Dawn M.
Wellman a b , Jim A. Kelly a b & Irina P. Smoliakova a
a Chemistry Department , University of North
Dakota , Grand Forks, ND, 58202, USA
b NSF-REU program participants
Published online: 04 Dec 2007.
To cite this article: Leonid N. Koikov , Mingming Han , Dawn M. Wellman , Jim A.
Kelly & Irina P. Smoliakova (2000) The Use of tert-Butyl Vinyl Ether in Stepwise
Electrophilic Addition Reactions, Synthetic Communications: An International Journal
for Rapid Communication of Synthetic Organic Chemistry, 30:18, 3451-3464, DOI:
10.1080/00397910008086984
To link to this article: http://dx.doi.org/10.1080/00397910008086984
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