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.
A New Route to 2(5H)-Furanones via Ruthenium-catalysed Oxidative Cyclocarbonylation of Allylic Alcohols
Kondo, Teruyuki,Kodoi, Kouichi,Mitsudo, Take-aki,Watanabe, Yoshihisa
, p. 755 - 756 (2007/10/02)
Several 2(5H)-furanoses are readily prepared in moderate to high yields by ruthenium-catalysed oxidative cyclocarbonylation of 1,1-disubstituted allyl alcohols.
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.
Reaction of Olefins with Malonic Acid Derivatives in the Presence of Manganese(III) Acetate
Fujimoto, Noriyuki,Nishino, Hiroshi,Kurosawa, Kazu
, p. 3161 - 3168 (2007/10/02)
The reaction of methylmalonic acid with mono- and disubstituted olefins in the presence of manganese(III) acetate yielded 2-carboxy-2-methyl-4-butanolides in moderate to good yields.The reactions of bromomalonic acid and chloromalonic acid with a variety
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.
REACTION DES ORGANOLITHIENS AVEC L'ETHOXY-5 DIHYDRO-2,5 FURANNONE-2. PREPARATION DE δ-2 BUTENOLIDES DISUBSTITUES SUR LE CARBONE-4.
Machado-Araujo, Francisca W. L.,Gore, Jacques
, p. 2897 - 2904 (2007/10/02)
Organolithium react with 5-ethoxy 2,5 dihydro-furan-2-one 1, easily obtained by photoxidation of furfural, leading selectively to 5-hydroxy-2,5-dihydro-furans 4 or to 5-ethoxy-2,5 dihydro-furans 5 disubstituted on carbon 4; the oxydation of the hemi-acetals 4 transforms them with good yields in Δ-2 butenolides disubstituted on carbon 4.
Lactones, I: Synthesis of Dihydroxylated Diphenylethanamines via &α-Amino-&γ-lactones
Lehmann, Jochen
, p. 241 - 249 (2007/10/02)
Treatment of α-amino-γ-lactones with phenyllithium yields the 2-amino-1,1-diphenylalkane-1,4-diols 2a-f which can be classified as dihydroxylated diphenylethanamines.
Methyleneketones and Methylenecarbenes. XVI. The Formation of Diphenylfuran-2-ones and 3-Phenylphthalide as Minor Products of the Pyrolysis of Diphenylmethyl Propiolate
Brown, Roger F. C.,Eastwood, Frank W.,Chaichit, Narongsak,Gatehouse, Bryan M.,Pfeiffer, Jan M.,Woodroffe, David
, p. 1467 - 1481 (2007/10/02)
The formation of a mixture of lactones as a minor product of the flash vacuum pyrolysis of diphenylmethyl propiolate (1) has been investigated further.The diphenylfuran-2-ones (3), (4), and (5) are shown to be formed through an intramolecular insertion reaction of the methylenecarbene (2), formed from (1) at 640 deg, which leads to 5,5-diphenylfuran-2(5H)-one (3) as the primary product. 3-Phenylphthalide (8) is apparently formed by intramolecular Diels-Alder addition of the CC bond of (1) to one phenyl ring which acts as the diene component, followed by loss of acetylene from an intermediate barrelene derivative (10).This is confirmed by a deuterium labelling experiment. 1-Phenyl-2-benzoxepin-3(1H)-one (7), considered at first as a possible intermediate in the pyrolysis of (1), is synthesized in six steps from 2-aminobenzophenone, and its X-ray structure determination is reported.On pyrolysis at 640 deg/0.07 mm (7) decarbonylates smoothly to give 2-vinylbenzophenone.
A FACILE AND GENERAL ROUTE TO 4-SUBSTITUTED-2 BUTENOLIDES
Canonne, Persephone,Akssira, Mohamed,Lemay, Gilles
, p. 2611 - 2614 (2007/10/02)
Grignar reagents react with 7-oxabicyclohept-5-ene-2,3-dicarboxylic anhydride and produce in high yields the corresponding substituted bicyclo-γ-butanolides.These lactones produce the title compounds by retro Diels-Alder reaction during distillation.
