70303-25-2Relevant academic research and scientific papers
Reduction of benzylic alcohols and α-hydroxycarbonyl compounds by hydriodic acid in a biphasic reaction medium
Dobmeier, Michael,Herrmann, Josef M.,Lenoir, Dieter,Koenig, Burkhard
supporting information; experimental part, p. 330 - 336 (2012/05/20)
The synthetic protocol for the reduction of alcohols to hydrocarbons by using hydriodic acid, first described by Kiliani more than 140 years ago, was improved to be more applicable to organic synthesis. Instead of a strongly acidic, aqueous solution, a biphasic toluene-water reaction medium was used, which allowed the conversion of primary, secondary and tertiary benzylic alcohols, in good yields and short reaction times, into the corresponding hydrocarbons. Red phosphorous was used as the stoichiometric reducing agent. Keto, ester, amide or ether groups are tolerated, and catalytic amounts of hydriodic acid (0.2 equiv) in the presence of 0.6 equiv phosphorous are sufficient to achieve conversion.
Sulfoxides in Julia-Lythgoe olefination: Efficient and stereoselective preparation of di-, tri-, and tetrasubstituted olefins
Pospisil, Jiri,Pospisil, Tomas,Marko, Istvan E.
, p. 2373 - 2376 (2007/10/03)
(Chemical Equation Presented) A novel modification of the classical Julia-Lythgoe olefination, using sulfoxides instead of sulfones, affords, after in situ benzoylation and Sml2/HMPA- or DMPU-mediated reductive elimination, 1,2-di-, tri-, and tetrasubstituted olefins in moderate to excellent yields and E/Z selectivity. The conditions are mild, and the procedure is broadly applicable.
Sulfoxide-modified Julia-Lythgoe olefination: Highly stereoselective di-, tri-, and tetrasubstituted double bond formation
Pospisil, Jiri,Pospisil, Tomas,Marko, Istvan E.
, p. 1953 - 1969 (2007/10/03)
A novel modification of the classical Julia-Lythgoe olefination, using sulfoxides instead of sulfones, affords, after in situ benzoylation and SmI 2/HMPA or SmI2/DMPU-mediated reductive elimination, 1,2-di-, tri- and tetrasubstituted olefins in moderate to good yields and E/Z selectivity. The conditions are mild and the procedure is widely applicable. The reaction mechanism was studied and a general model, describing the reaction selectivity, is proposed.
A Convergent Method for the Stereoselective Synthesis of Trisubstituted Alkenes
Martin, Stephen F.,Daniel, Dilon,Cherney, Robert J.,Liras, Spiros
, p. 2523 - 2525 (2007/10/02)
A method for the stereoselective, convergent synthesis of trisubstituted alkenes has been developed.The procedure features the synthesis of allylic alcohols 9 by coupling an aldehyde with a vinyl organometallic reagent.Treatment of 9 with carbon disulfide
Formylation and Acylation Reactions Catalysed by Trifluoromethanesulphonic Acid
Booth, Brian L.,El-Fekky, Teymour A.,Noori, Ghazi F. M.
, p. 181 - 186 (2007/10/02)
Regioselective formylation of toluene, m- and p-xylene, and mesitylene has been achieved by carbonylation in trifluoromethanesulphonic acid at CO pressures of 90-125 atm.In the case of cumene, the formylation reaction is in competition with disproportionation to form di- and tri-isopropylbenzenes, leading to a complex product mixture.Slow addition of cyclohexene or cyclopentene to a mixture of benzene and CF3SO3H under a high CO pressure affords 4-cyclohexylbenzaldehyde and 4-cyclopentylbenzaldehyde in 34percent and 33percent yieds, respectively, while 2-methylbut-1-ene gives 2,2,3-trimethylindanone (39percent) under similar conditions.When cyclohexene is mixed with the acid under carbon monoxide (120 atm) before addition of benzene the major products are cyclohexyl phenyl ketone and cyclohexenyl cyclohexyl ketones.
