7477-77-2Relevant articles and documents
Copper-catalyzed aerobic C-C bond cleavage of lactols with N-hydroxy phthalimide for synthesis of lactones
Tnay, Ya Lin,Chiba, Shunsuke
supporting information, p. 873 - 877 (2015/04/14)
The transformation of cyclic hemiacetals (lactols) into lactones has been achieved by Cu-catalyzed aerobic C-C bond cleavage in the presence of N-hydroxy phthalimide (NHPI). The present process is composed of a multistep sequence including a) formation of exo-cyclic enol ethers by dehydration; b) addition of phthalimide N-oxyl radical to the enol ethers followed by trapping of the resulting C-radicals with molecular oxygen to form peroxy radicals; c) reductive generation of oxy radicals and subsequent β-radical fragmentation to generate lactones.
METHYL 3-PHENYLSULPHONYL ORTHOPROPIONATE: AN EFFICIENT REAGENT FOR THE SYNTHESIS OF γ-LACTONES AND BUTENOLIDES
Carretero, Juan Carlos,Lombaert, Stephane De,Ghosez, Leon
, p. 2135 - 2138 (2007/10/02)
Treatment of methyl 3-phenylsulphonyl orthopropionate with n-BuLi gives the corresponding carbanion which reacts with aldehydes or ketones to yield β-phenylsulphonyl-γ-lactones.Base-catalysed elimination yields α,β or β,γ-butenolides.
ETUDE DE L'ACTION DES ALKYLMAGNESIENS PRIMAIRES ET ARYLMAGNESIENS SUR LES ANHYDRIDES TRICYCLIQUES PONTES
Canonne, P.,Akssira, M.,Fytas, G.
, p. 1809 - 1816 (2007/10/02)
The reaction of primary alkyl and aromatic Grignard reagents with bridged tricyclic dicarboxylic anhydrides gives the corresponding dialkylated tricyclic lactones via di-addition process.The lactones were transformed by retro-Diels-Alder reaction into 4,4-dialkylated butenolides.
