22914-08-5Relevant articles and documents
Ionic liquid promoted regio- And stereoselective addition of thiols to alkynes and alkenes under organic solvent free condition - A green reaction
Ranu, Brindaban C.,Chattopadhyay, Kalicharan,Ghosh, Sudip,Jana, Ranjan
experimental part, p. 1199 - 1204 (2009/12/31)
A simple ionic liquid, l-methyl-3-pentylimidazolium fluoroborate, [pmIm]BF4, promotes anti-Markovnikov addition of thiols to alkynes providing (Z)- and (E)-vinyl sulfides stereoselectively. The addition of thiols to alkenes in presence of another ionic liquid, [pmim]Br proceeds through anti-Markovnikov manner, whereas the addition to vinyl ethers and acetates occurs at more electrophilic C-2 position adjacent to oxygen. The products are obtained in high yields.
Nucleophilic substitution by Grignard reagents on sulfur mustards
Converse, Antonella,Saaidi, Pierre-Loic,Sharpless, K. Barry,Finn
, p. 7336 - 7339 (2007/10/03)
With proper activation of the leaving group, sulfur mustards react with Grignard reagents with neighboring group participation of the sulfur atom. 2,6-Dichloro-9-thiabicyclo[3.3.1]nonane is especially useful in this regard, providing clean reactivity with organomagnesium nucleophiles on a topologically constrained scaffold.
Anti-Markovnikov addition of thiols across double bonds catalyzed by H- Rho-zeolite
Kumar, Pradeep,Pandey, Rajesh Kumar,Hegde, Vishnumurthy R.
, p. 1921 - 1922 (2007/10/03)
A variety of olefins react with thiols in the presence of a catalytic amount of H-Rho-zeolite to afford the corresponding anti-Markovnikov addition products in good to excellent yields.
Novel reaction of bis(trifluoromethyl)disulfide with organolithium reagents
Munavalli, S.,Rossman, D. I.,Rohrbaugh, D. K.,Ferguson, C. P.
, p. 155 - 161 (2007/10/02)
The reaction of bis(trifluoromethyl) disulfide with organolithium reagents at -78 deg C results in simultaneous scission of both the C-S and S-S bonds.Under similar conditions, the alkyl and aryl disulfides undergo only S-S bond cleavage.This unusual behavior of bis(trifluoromethyl) disulfide is due to the presence of the trifluoromethyl function.The product distribution, the mechanism of bond fission and the mass spectral data of compounds thus formed are presented in this paper.
THIOL ESTER IN ORGANIC SYNTHESIS XV. REDUCTION WITH TETRABUTYLAMMONIUM BOROHYDRIDE
Liu, Hsing-Jang,Luo, Weide
, p. 387 - 392 (2007/10/02)
Treatment of thiol ester with tetrabutylammmonium borohydride in refluxing chloroform gave rise to the corresponding alcohols.
One-Flask Synthesis of Sulfides from Alcohols and Alkyl Halides Using Benzoxazoline-2-thione
Takeuchi, Yasuo,Sakagawa, Keiko,Kubo, Masumi,Yamato, Masatoshi
, p. 1323 - 1327 (2007/10/02)
The synthesis of sulfides from alcohols and benzoxazoline-2-thione (I) was studied to establish its generality and the mechanism of the reaction.A one-flask synthesis of sulfides from alcohols was developed.According to this procedure, various sulfides were prepared without the use of illsmelling thiols.Moreover, partial sulfenylation of diols to give sulfenyl alcohols was achieved.Keywords - one-flask synthesis; benzoxazoline-2-thione; partial sulfenylation; sulfide; sulfenyl alcohol
A Facile One-pot Synthesis of Sulfides from Alkyl Halides and Alcohols Using Tetramethylthiourea
Fujisaki, Shizuo,Fujiwara, Isamu,Norisue, Yasumasa,Kajigaeshi, Shoji
, p. 2429 - 2430 (2007/10/02)
Sulfides can be readily prepared under mild conditions by a reaction of tetramethylthiourea with alkyl halides and alcohols in the presence of sodium hydride in satisfactory yields.The scope and limitation of this method are also presented.
