82707-19-5Relevant academic research and scientific papers
Neutral sulfur nucleophiles: Synthesis of thioethers and thioesters by substitution reactions of N-heterocyclic carbene boryl sulfides and thioamides
Pan, Xiangcheng,Curran, Dennis P.
supporting information, p. 2728 - 2731 (2014/06/09)
Newly discovered boryl sulfides and N-borylthioamides are shown to serve as neutral sources of sulfur nucleophiles in substitutions reactions. For example, heating of diMe-Imd-BH(SPh)2 with benzyl bromides, primary bromides, or acid chlorides provides the corresponding thioethers or thioesters in high yields. Likewise, N-phenyltetrazole thioethers/esters are made from a readily available N-borylthionotetrazole. The formation of the boryl sulfide and its onward nucleophilic substitution can be telescoped down to a one-pot reaction whose components are an NHC-borane (NHC-BH3), a disulfide, and an electrophile.
Sequential one-pot reactions of thioformates with lithium silylacetylides, arylmagnesium halides, and electrophiles leading to formation of propargyl sulfides
Murai, Toshiaki,Ohashi, Takayuki,Shibahara, Fumitoshi
supporting information; experimental part, p. 70 - 71 (2011/05/07)
One-pot reactions of thioformates with lithium silylacetylides, arylmagnesium halides, and electrophiles that produce propargyl (2-propynyl) sulfides are described. The pathway for this process begins with addition of lithium (trimethylsilyl)acetylide to the thioformate C=S carbon. This step is followed by addition of the arylmagnesium halide to the sulfur atom of the C=S group in the in situ generated propynethial. The intermediacy of the propynethial in this process was confirmed by trapping through a Diels-Alder reaction with cyclopentadiene.
Titanacyclobutenes or titanium vinyl carbene complexes? Reactivity of organotitanium species generated by the reaction of γ-chloroallyl sulfides with a titanocene(II) reagent
Shono, Tomohiro,Kurashige, Rie,Mukaiyama, Ryo,Tsubouchi, Akira,Takeda, Takeshi
, p. 4074 - 4080 (2008/02/08)
The reactivity of the organotitanium species generated by the reductive titanation of γ-chloroallyl sulfides with the titanocene(II) reagent [Cp2Ti{P(OEt)3}2] was studied. The organotitanium species formed from α-monosubstituted γ-chloroallyl sulfides reacted with 1,5-diphenylpentan-3-one and styrene to produce conjugated dienes and vinyl cyclopropanes as major products, thus suggesting the formation of vinyl carbene complexes as intermediates. On the contrary, the organotitanium species generated from acyclic β,γ-disubstituted γ-chloroallyl sulfides revealed titanacyclobutene-like reactivity, and their reaction with 1,5-diphenylpentan-3-one produced homoallyl alcohols. These organotitanium species did not react with styrene, but did react with dichlorophenylphosphine to afford phosphacyclobutenes. In the case of β-monosubstituted, γ-monosubstituted, and α,γ- disubstituted γ-chloroallyl sulfides, the organotitanium species reacted with both 1,5-diphenylpentan-3-one and styrene. The former reaction produced homoallyl alcohols and the latter gave vinyl cyclopropanes or unconjugated dienes. These results suggest that titanacyclobutenes and/or titanium vinyl carbene complexes are produced by the reductive titanation of γ-chloroallyl sulfides depending on their substitution patterns.
One-pot practical preparation of novel propargylic aryl and heteroaryl sulfides and sulfones
Bonini, Carlo,Chiummiento, Lucia,Videtta, Valeria
, p. 3067 - 3070 (2007/10/03)
A one-pot preparation of functionalized propargylic aryl and hetero aryl sulfides from primary alcohols and thiols through the formation of the corresponding iodide or tosylate compounds is presented. The corresponding sulfones are prepared by subsequent
Synthesis and cytotoxicity of 3-(hetarylthio)-1-propynyl-(trimethyl)silanes
Abele,Abele,Rubina,Dzenitis,Arsenyan,Shestakova,Nesterova,Domracheva,Popelis,Grinberga,Lukevics
, p. 867 - 872 (2007/10/03)
We have developed a two-step method for synthesis of 3-(hetarylthio)-1-propynyl(trimethyl)silanes from thiols in a phase-transfer catalysis system HC≡CCH2Br-solid K2CO3-18-crown-6-toluene followed by reaction with n-BuLi-Me3SiCl in ether or THF. We have observed that 3-[1,3-bis(trimethylsilyl)-2-propynyl] thioindole displays high cytotoxicity in HT-1080 and MG-22A tumor cell lines.
Ruthenium-catalyzed S-propargylation of thiols enables the rapid synthesis of propargylic sulfides
Kondo, Teruyuki,Kanda, Yusuke,Baba, Atsushi,Fukuda, Kenji,Nakamura, Ayako,Wada, Kenji,Morisaki, Yasuhiro,Mitsudo, Take-aki
, p. 12960 - 12961 (2007/10/03)
A new and highly efficient catalytic system based on CpRuClL2 is proposed for the S-propargylation of thiols by propargylic carbonates under neutral conditions, in which specific requirements inherent to the different reactivities of aliphatic and aromatic thiols are achieved by tuning both the nature of the ancillary ligand L and the experimental conditions. Copyright
3-Arylthio- and 3-aroxy-1-propynes and their reactions with amines
Bogoradovskii,Maksimov,Zubova
, p. 1167 - 1172 (2007/10/03)
3-Arylthio and 3-aroxy-1-propynes can be prepared by reaction of substituted 3-bromo-1-propynes with arylthio- and aroxytrimethylstannanes. Stannylation of 3-arylthio-1-trimethylsilyl-1-propynes with diethyl(trimethylslannyl)amine is accompanied by cleavage of the Si-Csp bond.
Substituted propargylic sulfoxides: synthesis and -sigmatropic rearrangement in the presence of thiophilic reagents
Baudin, J. B.,Julia, S. A.,Lorne, R.
, p. 440 - 456 (2007/10/02)
The allenic sulfoxides 2 and 12 were converted into the substituted propargylic sulfoxides 3 and 13, respectively, by deprotonation with methyl lithium and reaction with electrophilic reagents.Smooth thermal -sigmatropic rearrangement of 3 and 13, using 2-mercapto-1-methylimidazole to desulfurize the intermediate allenic sulfenate XVa, yielded the corresponding conjugated enones 10.The possible reaction mechanism for these two transformations were examined. Key words: Allenic sulfoxides; propargylic sulfoxides; organolithium compounds adjacent to sulfoxides; -sigmatropic rearrangement; desulfurization; α,β-unsaturated enones; furanes.
Synthesis of ethynylcyclopropanes from epoxides
Narjes,Schaumann
, p. 1168 - 1170 (2007/10/02)
The title compounds are prepared by an efficient one-pot reaction involving ring-opening of an epoxide with lithium 3-trimethylsilyl-1-phenylthio-2-propyn-1-ide, tosylation of the intermediate alkoxide, and finally deprotonation. In an alternative approac
