The Use of tert-Butyl Vinyl Ether in Stepwise Electrophilic Addition Reactions

LN Koikov, M Han, DM Wellman, JA Kelly…

Index: Koikov, Leonid N.; Han, Mingming; Wellman, Dawn M.; Kelly, Jim A.; Smoliakova, Irina P. Synthetic Communications, 2000 , vol. 30, # 18 p. 3451 - 3464

Full Text: HTML

Citation Number: 5

Abstract

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 CC 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.

Related Articles:

Reactions of nitronates derived from simple nitro alkanes with some thio-stabilized cationic intermediates

[Lyapkalo; Lazareva; Dil'man; Ioffe; Smit Russian Chemical Bulletin, 1999 , vol. 48, # 3 p. 488 - 494]

Synthesis, docking, and in vitro activity of thiosemicarbazones, aminoacyl-thiosemicarbazides and acyl-thiazolidones against Trypanosoma cruzi

[Leite, Ana Cristina Lima; de Lima, Renata Souza; Moreira, Diogo Rodrigo de M.; Cardoso, Marcos Verissimo de O.; Gouveia de Brito, Ana Carolina; Farias dos Santos, Luciene Maria; Hernandes, Marcelo Zaldini; Kiperstok, Alice Costa; de Lima, Ricardo Santana; Soares, Milena B.P. Bioorganic and Medicinal Chemistry, 2006 , vol. 14, # 11 p. 3749 - 3757]

More Articles...