- Catalyst-free imidation of allyl sulfides with chloramine-T and subsequent [2,3]-sigmatropic rearrangement
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A facile synthesis of various allyl sulfonamides based on imidation of allyl sulfides with chloramine-T and subsequent [2,3]-sigmatropic rearrangement has been achieved without metal catalysts. The reaction completes smoothly within 10 min, providing excellent yields in environment friendly solvent of alcohol. Functional groups such as bromine, hydroxyl, protected amido and aldehyde are tolerant under this condition.
- Jiang, Yubo,Mo, Fanyang,Qiu, Di,Kuang, Chunxiang,Zhang, Yan,Wang, Jianbo
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p. 2029 - 2035
(2012/11/07)
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- One-pot reductive sulfenylation and thiocyanation of carbonyl compounds in ionic liquid media
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The first example of an efficient one-pot reductive sulfenylation and thiocyanation of carbonyl compounds in environmentally benign ionic liquid (IL) media is reported. The process involves reduction of carbonyl compounds with NaBH4 in the IL [bmim]BF4 followed by I2-catalyzed reaction of the resulting alcohols with aromatic/aliphatic thiols or ammonium thiocyanate in the same vessel to afford sulfides or thiocyanates, respectively, in excellent yields (78-93%). Notably, the protocol precludes the necessity to prepare and isolate the intermediate alcohols in a separate step as they are formed in situ, and the IL used can be recycled easily for further use without any loss of efficiency. Copyright
- Yadav, Lal Dhar S.,Garima,Kapoor, Ritu
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experimental part
p. 100 - 112
(2011/03/17)
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- Reactions of 2-(α-Haloalkyl)thiiranes with nucleophilic reagents: V.* Reactions of 2-(α-chloroalkyl)thiiranes with organolithium compounds
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2-(α-Haloalkyl)thiiranes reacted with methyl-, butyl-, and phenyllithium to give the corresponding allyl sulfides. The reactions of diastereoisomeric erythro-and threo-2-(1-chloroethyl)thiiranes with phenyllithium were stereospecific, and they afforded (E)-and (Z)-1-phenylsulfanylbut-2-enes, respectively. 3-Chloromethyl-2,2- dimethylthiirane and phenyllithium gave rise to a mixture of 3-methyl-3-phenylsulfanylbut-1-ene and 3-methyl-1-phenylsulfanylbut-2-ene. The reactions of 2-chloromethylthiiranes with phenyllithium and methyllithium in the presence of a catalytic amount of copper(I) iodide (10 mol %) led to the formation of substituted thiiranes as the major products. Mechanisms of the observed transformations are discussed. Pleiades Publishing, Ltd., 2010.
- Tomashevskii,Sokolov,Potekhin
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experimental part
p. 1822 - 1825
(2011/04/17)
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- A new approach to reductive deprotection of thioethers with a low-valent titanium reagent
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Low-valent titanium mediated cleavage of carbon-sulphur bond is reported. This has resulted in an efficient and mild protocol for the deprotection of allyl/benzyl thioethers under reductive condition and with good yields. Deprotection can be performed regio- and chemo-selectively in the presence of acid, ester and N-benzyl/allyl functionalities and is general for aliphatic and aromatic precursors.
- Shadakshari,Talukdar,Chattopadhyay
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p. 1007 - 1010
(2007/10/03)
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- NUCLEOPHILIC THIYLATION OF ALLYL HALIDES IN THE PRESENCE OF PHASE-TRANSFER CATALYSTS
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A study was carried out on the thiylation of allyl halides by sodium sulfide nonahydrate and 1-butanethiol in the presence of tetrabutylammonium bromide and polyglycol as phase-transfer catalysts leading to the formation of allyl sulfides.The physical constants, spectra characteristics and yields are given for the thiylation products.
- Tolstikov, G. A.,Kanzafarov, F. Ya.,Kanzafarova, S. C.,Singizova, V. Kh.
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p. 1261 - 1266
(2007/10/02)
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