56569-76-7Relevant academic research and scientific papers
Alkyl Migration in Competition with Phenylthio Migration in the Acid-catalysed Rearrangement of Alcohols
Hannaby, Malcolm,Warren, Stuart
, p. 3007 - 3014 (2007/10/02)
Sulfonate derivatives of conformationally rigid syn-2-phenylthiocyclohexanols, which are prevented from phenylthio migration by stereochemistry, rearrange slowly by alkyl migration or ring contraction.In contrast to other electronegative groups, phenylthio slows the reaction down but allows migration of other groups.
UNUSUAL CONJUGATE ADDITION OF ORGANOLITHIUM REAGENT TO α,β-UNSATURATED KETONE
Maruoka, Keiji,Nonoshita, Katsumasa,Yamamoto, Hisashi
, p. 5723 - 5726 (2007/10/02)
The conjugate addition of organolithium reagent to α,β-unsaturated ketone has been accomplished with methylaluminum bis(2,6-di-tert-butyl-4-alkylphenoxide) (MAD and MAT).Here combination of alkyllithium and MAD (or MAT) constitutes an amphiphilic system that allows to exhibit unusual selectivity in the alkylation of enones with alkyllithium.
ALKYL MIGRATION INCLUDING RING CONTRACTION FROM A MIGRATION ORIGIN BEARING A PHENYLTHIO (PhS) GROUP
Hannaby, Malcolm,Warren, Stuart
, p. 1069 - 1072 (2007/10/02)
Alkyl shifts occur from tertary C atoms bearing a PhS group if PhS migration is prevented, but are retarded by the PhS group: the transition state has a cation-like migration terminus with little, if any, alkyl participation.
CROSS-COUPLING REACTION BETWEEN ENOL PHOSPHATES AND ORGANOALUMINIUM COMPOUNDS IN THE PRESENCE OF PALLADIUM(0) CATALYST.
Takai,Sato,Oshima,Nozaki
, p. 108 - 115 (2007/10/02)
The title reaction in the presence of a catalytic amount of tetrakis(triphenylphosphine)palladium(0) affords alkylative coupling products in good to excellent yields in 1,2-dichloroethane at room temperature. This coupling reaction under C(sp**2)-O cleavage proceeds stereospecifically. The reaction does not affect a coexisting vinyl sulfide group. This feature enables 1,2- and 1,3-carbonyl transposition with or without alkylation via phenylthio-substituted enol phosphates.
Fluoride-Mediated Reactions of Enol Silyl Ethers. Regiospecific Monoalkylation of Ketones
Kuwajima, Isao,Nakamura, Eiichi,Shimizu, Makoto
, p. 1025 - 1030 (2007/10/02)
Treatment of enol silyl ethers with alkyl halides in the presence of benzyltrimethylammonium fluoride and molecular sieves at room temperature gives the corresponding monoalkylated products with high regiospecificity.In most cases no polyalkylated products formed in the reaction.The alkylation reaction is highly chemospecific: esters, epoxides, and even ketones survive the reaction conditions.The reactions of various cyclohexanone derivatives proceed with the preferential axial attack of the electrophile.
Pd(O) PROMOTED ALKYLATION OF ENOL PHOSPHATES WITH ORGANOALUMINIUM COMPOUNDS AND ITS SYNTHETIC APPLICATIONS
Sato, Mitsuyoshi,Takai, Kazuhiko,Oshima, Koichiro,Nozaki, Hitosi
, p. 1609 - 1612 (2007/10/02)
Keto carbonyl 1,2- and 1,3-transpositions with and without alkylation of the substrate are described together with ketone synthesis from thiocarboxylic S-ester.
HYDROGENOLYSE EN PHASE LIQUIDE SUR Pd/C DES EPOXYDES DU CARVOMENTHENE ET DU LIMONENE
Accrombessi, G.,Geneste, P.,Olive, J.-L.,Pavia, A. A.
, p. 3135 - 3140 (2007/10/02)
Hydrogenolysis over Pd/C of cis and trans epoxides of carvomenthene and limonene give a mixture of hydrocarbons, secondary and tertiary alcohols, and ketones in proportions dependent upon the nature of the starting material.In the limonene epoxides, the extracyclic double bond plays an important role in the opening of the oxirane ring through a common unsaturated tertiary alcohol intermediate by double bond migration, hydrogenation of which leads to the products.For the carvomenthene epoxides the results are similar to those found in the 4-t-butyl series with competition between cis addition and trans addition of hydrogen.The presence of the isopropenyl group leads to slower reaction rates in comparison with t-butyl analogues.
