87156-77-2Relevant academic research and scientific papers
Enantioselective allylic thioetherification: The effect of phosphoric acid diester on iridium-catalyzed enantioconvergent transformations
Roggen, Markus,Carreira, Erick M.
, p. 8652 - 8655 (2012/10/08)
You'll take the high road and I'll take the low road: Enantioenriched allylic thioethers have been synthesized from chiral racemic allylic alcohols. The combination of an Ir-(P,alkene) complex and dibutyl phosphoric acid are required to attain high select
Fast ruthenium-catalysed allylation of thiols by using allyl alcohols as substrates
Zaitsev, Alexey B.,Caldwell, Helen F.,Pregosin, Paul S.,Veiros, Luis F.
scheme or table, p. 6468 - 6477 (2010/02/28)
The allylation of aromatic and aliphatic thiols, by using allyl alcohols as substrates, requires only minutes at ambient temperature with either a Ru Iv catalyst, [Ru(Cp*)(n3CH5)(CH 3CN)2](PF6)2 (2; Cp* = pentamethylcyclopentadienyl) or a combination of [Ru(Cp*)(CH 3CN)3](PF6) and camphor sulfonic acid. Quantitative conversion is normal and the catalyst possesses high functional-group tolerance. The use of [Ru(Cp*)(CH3CN) 3](PF6) alone affords poor results. A comparison is made to the results from catalytic runs based on the use of carbonates rather than alcohols, by using 2 as the catalyst, and it is shown that the products from the alcohols are formed faster, so there is no advantage in using a carbonate substrate. The observed branched-to-linear (b/1) ratios when using substituted alcohols decrease with time suggesting that the catalysts isomerise the products. A new methodology from which one can select the desired isomeric product is proposed. DFT calculations and NMR spectroscopic measurements, by using an arene sulfonic acid as co-catalyst, suggest that 6-complexes are not relevant for the catalytic system. Moreover, the DFT results indicate that l)any rf-complexes from the acids RC6H4SO 3H result from deprotonation of the acid, 2) complexation of the thiol, via the deprotonated sulfur atom, is preferred over complexation of the O atom of the sulfonate, RC6H4SO3and 3) a sulfonate O-atom complex will be difficult to detect.
Direct synthesis of thioethers from sulfonyl chlorides and activated alcohols
Martin, Michael T,Thomas, Alford M,York, Douglas G
, p. 2145 - 2147 (2007/10/03)
An efficient, safe one-pot synthesis of thioethers from aromatic sulfonyl chlorides and activated alcohols has been developed under non-aqueous conditions.
Molecular orbital studies on pericyclic reactions of cinnamyl xanthates in β-cyclodextrin cavities
Eto,Kubota,Nakagawa,Yoshitake,Harano
, p. 1652 - 1659 (2007/10/03)
The solid β-cyclodextrin (β-CyD) complex of O-cinnamyl S-methyl dithiocarbonates (xanthate, 1a), upon heating at 45°C, underwent asymmetric [3,3]-sigmatropic rearrangement to give the optically S-(1-phenylallyl) S-methyl dithiocarbonate (2a) with 60% ee.
Novel Tandem Conjugate Addition-Ramberg-B?cklund Rearrangements
Evans, Paul,Taylor, Richard J. K.
, p. 1043 - 1044 (2007/10/03)
A novel tandem process is reported for the preparation of allylic amines, ethers and sulfides from α-bromo-α,β-unsaturated sulfones; this process is believed to proceed via an initial conjugate addition followed by proton exchange and Ramberg-Ba?cklund rearrangement.
Stereoselective formation of allylic sulfides via two sequential [3,3]-sigmatropic rearrangements of allylic xanthates and its mechanistic aspects
Harano,Ohizumi,Misaka,Yamashiro,Hisano
, p. 619 - 624 (2007/10/02)
O-(2-Alkenyl) S-alkyl dithiocarbonates (allylic xanthates) were pyrolyzed to give 2-alkenyl alkyl sulfides (allylic sulfides) via the corresponding allylically isomeric S-(2-alkenyl) S-alkyl dithiocarbonates. The reaction follows the first-order rate law
An Odorless Preparative Method of Sulfides and Thiocarboxylic S-Esters Using 3-(Alkylthio)-1,2-benzisothiazole 1,1-Dioxide
Yamada, Hiroyuki,Kinoshita, Hideki,Inomata, Katsuhiko,Kotake, Hiroshi
, p. 949 - 950 (2007/10/02)
It was found that sodium salt of 1,2-benzisothiazole-3(2H)-thione 1,1-dioxide (thiosaccharin) readily reacted with alkyl halide affording 3-(alkylthio)-1,2-benzisothiazole 1,1-dioxide (3).Treatment of 3 with piperidine produces the corresponding alkanethiol in situ quantitatively and subsequent treatment with various electrophiles gives the corresponding sulfides and thiocarboxylic S-esters in good yields.
Synthesis by SO2 Extrusion: Photochemical and Thermal Reactions of Cinnamyl Benzyl Sulfone
Wylie, Philip L.,Prowse, K. Spencer,Belill, Mark A.
, p. 4022 - 4025 (2007/10/02)
The photochemistry and pyrolytic behavior of trans-cinnamyl benzyl sulfone have been investigated.Direct photolysis in benzene gives high yields of the SO2 extrusion products 3,4-diphenyl-1-butene and cis- and trans-1,4-diphenyl-1-butene.Addition of trans-piperylene to the photolysis substantially reduces the amount of cis-1,4-diphenyl-1-butene formed.Photolysis in acetone gives primarily trans-cis isomerization, though minor amounts of the SO2 extrusion products and bibenzyl were also formed.Flash vacuum pyrolysis of cinnamyl benzyl sulfone gave only minor amounts o f the SO2 extrusion products; these were shown to be unstable under the conditions of pyrolysis.Instead, indene, styrene, bibenzyl, and toluene were formed.Pyrolysis of 1,4-diphenyl-1-butene gave these same products.
