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Stage #1: thiophenol With sodium hydroxide In methanol at 70℃; for 1h; Cooling with acetone-dry ice;
Stage #2: ethylene dibromide In methanol at 70℃; for 1h; Cooling;
2.2.1. 3,7-Dithianonane (BETP)
General procedure: Ethanethiol (30 mL, 400 mmol) was added dropwise to a saturatedsolution (50 mL) of NaOH in MeOH cooled in a dry-ice/acetone bath;the mixture was then stirred at 70 °C for 1 h, and then cooled againprior to dropwise addition of 1,3-dibromopropane (20.6 mL, 200 mmol)with stirring. After being warmed at 70 °C for 1 h, the solution waspoured into H2O (100 mL), and the oily, immiscible dithioether layerwas collected. The aqueous layer was extracted three times with Et2O(40 mL) portions, the organic residues being combined; the Et2O wasremoved by rotary evaporation, and the oily product was dried overMgSO4. Yield 21 g (64%).
With sodium hydroxide
With potassium hydroxide In ethanol Heating;
With potassium hydroxide 1.) EtOH, 2.) EtOH, a) RT, 2 h, b) reflux, 30 min; Multistep reaction;
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite In dichloromethane; water oxidation with various oxidants;
1: 2 % Spectr.
2: 98 % Spectr.
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; tetrabutyl-ammonium chloride; sodium hydrogencarbonate; potassium bromide In dichloromethane; water 0 deg C, 1 h, RT, 0.5 h;
With dihydrogen peroxide; acetic acid at 20℃; Title compound not separated from byproducts;
With dihydrogen peroxide In acetic acid at 20℃;
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0℃; for 0.5h; Inert atmosphere; optical yield given as %de;
4.3.1. General procedure for racemic oxidation for the development of chiral assays
General procedure: Sulfide (1 equiv) was dissolved in CH2Cl2 (1 M) and the solution was cooled to 0 °C. mCPBA (3.05 equiv for tris-sulfides, 2.05 equiv for bis-sulfides; 74% by weight) was then added, and the reaction mixture was stirred at 0 °C for 30 min. The crude mixture was poured into brine and aqueous 1 M NaOH was added to basify. This mixture was extracted twice with CH2Cl2 and the organic extracts were dried over Na2SO4. The solvent was removed in vacuo. The homochiral diastereomer was isolated by preparative TLC. For ligands 7b-e, the meso diastereomer could not be removed by chromatography, but separation was achieved during HPLC analysis
With dihydrogen peroxide In acetic acid at 20℃; Inert atmosphere;
In tetrahydrofuran mixing reactants in THF at -78°C, slow warming to room temp.; evapn. in vac., extn. with pentane, ether and finally acetone or CH2Cl2, concn., chromy. on Al2O3, purifn. by crystn., distn. or sublimation;
In ethanol; dichloromethane mixing soln. of Na2PdCl4 (in EtOH) and ligand (in CH2Cl2), refluxing (3 h); concn., filtration, washing (EtOH, ether), drying (vac.); elem. anal.;
acethylacetonato(1,5-cyclooctadiene)rhodium(I)[ No CAS ]
[ 622-20-8 ]
Rh{(C6H5)S(CH2)2S(C6H5)}(C7H8)(1+)*BF4(1-) = Rh{(C6H5)S(CH2)2S(C6H5)}(C7H8)BF4[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With trityl tetrafluoroborate In dichloromethane to a soln. of Rh complex in CH2Cl2, a soln. of the appropriate amt. of PhS(CH2)2SPh is added at 0°C; soln. concd. in vac., addn. of Et2O, compd. sepd.; recrystd. from dichloromethane/ether;
[(η(5)-cyclopentadienyl)Fe(CO)(P(OPh)3)(Cl)][ No CAS ]
[ 38117-54-3 ]
[ 3561-67-9 ]
[ 622-20-8 ]
[ 882-33-7 ]
lithium chloride[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
1: 95%
2: 43%
3: 30%
4: 25%
5: 31%
In tetrahydrofuran mixing reactants in THF at -78°C, slow warming to room temp. / further products; evapn. in vac., extn. with pentane, ether and finally acetone or CH2Cl2, concn., chromy. on Al2O3, purifn. by crystn., distn. or sublimation;
With hypophosphorous acid In 2-methoxy-ethanol all manipulations under N2; adding PhSCH2CH2SPh to a soln. of RuCl3*nH2O, refluxing (2 h), adding hypophosphorous acid after 1 h of reflux; evapg. (vac.), extg. (CH2Cl2), pptn. (adding Et2O);
In dichloromethane dropwise addn. of a CH2Cl2 soln. of the ethane to a CH2Cl2 soln. of the Pt complex with stirringreflux, 2 h, pptn.; filtration, washing (cold methanol, twice diethyl ether), drying under reduced pressure, elem. anal.;
With hypophosphorous acid In 2-methoxy-ethanol all manipulations under N2; adding PhSCH2CH2SPh to a soln. of RuBr3*nH2O, refluxing (2 h), adding hypophosphorous acid after 1 h of reflux; evapg. (vac.), extg. (CH2Cl2), pptn. (adding Et2O);
In dichloromethane addn. of stoichiometric amount of the ligand to the soln. of Pt(II) complex; pptn. with Et2O or n-hexane, cooling to -30 ° C, filtration, washing (n-hexane), air drying, elem. anal.;
In dichloromethane under N2; to a soln. of the Mo complex in CH2Cl2 was added the ligand, stirred for 2 h; solvent was removed in vac., redissolved in CH2Cl2, filtered, vol. was reduced, cooled to -17°C for 24 h; elem. anal.;
In dichloromethane under N2; to a soln. of the W-complex in CH2Cl2 was added the ligand, stirred for 2 h; solvent was removed in vac., redissolved in CH2Cl2, filtered, vol. was reduced, cooled to -17°C for 24 h; elem. anal.;
In dichloromethane under N2; to a soln. of the W-complex in CH2Cl2 was added the ligand, stirred for 3 h; solvent was removed in vac., redissolved in CH2Cl2, filtered, solvent was removed in vac., washed with ether; elem. anal.;
In tetrahydrofuran mixing reactants in THF at -78°C, slow warming to room temp. / further products; evapn. in vac., extn. with pentane, ether and finally acetone or CH2Cl2, concn., chromy. on Al2O3, purifn. by crystn., distn. or sublimation;
chloro(cyclo-octa-1,5-diene)hydrido[hydrogenbis(diphenylphosphinito)]iridium(III)[ No CAS ]
[ 622-20-8 ]
[1,2-bis(phenylthio)ethane]chlorohydrido[hydrogenbis(diphenylphosphinito)]iridium(III)[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
75%
In chloroform Ir-complex in CHCl3 was treated with ligand, shaken for 4 h, light petroleum was added; concd., recrystd. from CHCl3-ligh petroleum, washed with light petroleum, Et2O, dried in vac. at 60°C; elem. anal.;
[C6H5S(O)CHC6H5](1-)*Li(1+)=[C6H5S(O)CHC6H5]Li[ No CAS ]
[ 12100-38-8 ]
[ 38117-54-3 ]
[ 3561-67-9 ]
[ 622-20-8 ]
[ 882-33-7 ]
lithium chloride[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
1: 91%
2: 52%
3: 22%
4: 25%
5: 36%
In tetrahydrofuran mixing reactants in THF at -78°C, slow warming to room temp. / further products; evapn. in vac., extn. with pentane, ether and finally acetone or CH2Cl2, concn., chromy. on Al2O3, purifn. by crystn., distn. or sublimation;
In tetrahydrofuran mixing reactants in THF at -78°C, slow warming to room temp. / further products; evapn. in vac., extn. with pentane, ether and finally acetone or CH2Cl2, concn., chromy. on Al2O3, purifn. by crystn., distn. or sublimation;
In nitromethane under Ar, Cp2Ni and (PhSCH2)2 in MeNO2 treated with HBF4*Et2O at -30°C; cold ether added, solid purified by decantation and washing with cold ether, dried in vac. at -30°C and room temp.; elem. anal.;
In acetone N2-atmosphere; addn. of 2 equiv. of ligand to Ag-salt; evapn., trituration with ice-cold pentane, washing (pentane, Et2O), drying (vac.); elem. anal.;
[Mo(η(3)-C3H5)(CO)2(C6H5SCH2CH2SC6H5)][PF6][ No CAS ]
Yield
Reaction Conditions
Operation in experiment
50%
In acetone under Ar using Schlenk techniques; mixt. stirred for 3 h; solvent evapd. to dryness; residue washed (pentane) at -70°C; as oil at room temp.;
In dichloromethane Ar-atmosphere; stirring soln. of equimolar amts. of Mo-complex and HBF4 for 10 min, addn. of excess of PhSCH2CH2SPh, stirring for 1 h at room temp.; concn., pptn. on addn. of ether, recrystn. (CH2Cl2:Et2O); elem. anal.;
In dichloromethane all manipulations under dry N2; org. compd. added to soln. of Pd compd.,stirred at room temp. for 5 h; hexane added, concd., washed with hexane, dried in vac., recrystd, from CH2Cl2/hexane, elem. anal.;
In tetrahydrofuran (Ar); addn. of ligand to a suspn. of platinum complex in THF at -40°C, warming to room temp.; concn., addn. of Et2O, stirring for 2 d, filtration, washing with Et2O, drying in vac.; elem. anal.;
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