- One-pot oxidative bromination – Esterification of aldehydes to 2-bromoesters using cerium (IV) ammonium nitrate and lithium bromide
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A two-step, one-pot reaction of aldehydes with the CAN/LiBr oxidation system under solvent-free conditions followed by the addition of methanol affords methyl α-bromocarboxylates. The oxidation of aldehydes with methanol using this system gives only methyl esters. A facile method, which does not require special equipment, was developed for the synthesis of 2-bromoesters from aliphatic aldehydes with carbon chain lengths of 5–10 atoms.
- Nikishin, Gennady I.,Kapustina, Nadezhda I.,Sokova, Lyubov L.,Bityukov, Oleg V.,Terent'ev, Alexander O.
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supporting information
p. 352 - 354
(2017/01/03)
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- New free-radical halogenations of alkanes, catalysed by N-hydroxyphthalimide. Polar and enthalpic effects on the chemo- and regioselectivity
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Reactions of alkanes with different halogenating systems are compared in order to explore the reactivity of phthalimido-N-oxyl radical in hydrogen abstraction; the importance of polar effects is emphasised.
- Minisci, Francesco,Porta, Ombretta,Recupero, Francesco,Gambarotti, Cristian,Paganelli, Roberto,Pedulli, Gian Franco,Fontana, Francesca
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p. 1607 - 1609
(2007/10/03)
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- Electrochemical fluorination of several methyl and/or ethyl esters of morpholino-substituted carboxylic acids
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Seven methyl and/or ethyl esters of carboxylic acids (-CH2CH2C(O)OEt, -CH2CH2CH2C(O)OMe, -CH2CH2CH2C(O)OEt, -CH(C2H5)C(O)OMe, -CH(n-C3H7)C(O)OMe, -CH2CH2CH2CH2C(O)OEt and -CH2CH2CH2CH2CH2C(O) OEt) having a morpholino group were subjected to electrochemical fluorination (ECF). On ECF, the corresponding perfluoroacid fluorides bearing a perfluoromorpholino group were obtained in fair to good yields. Yields of the targeted perfluoromorpholino-containing perfluoroacid fluorides were influenced by the α-bond cleavage of the carboxylic acid and also by the kind of alkyl group of the carboxylic acid (the latter offering the possibility of cyclization side reactions). Perfluorooxolanes were formed as a major cyclization by-product from the ECF of morpholino-substituted carboxylic acids when the chain length of the alkyl group of the carboxylic acids had a carbon number of three or more and the structure of the alkyl group was branched in such a way as to allow cyclization. Perfluorodioxolanes were obtained in only small yields as the specific cyclization products when the ethyl esters of carboxylic acids were subjected to ECF. Spectroscopic data, as well as physicochemical properties, are described for the new perfluoroheterocyclic compounds with a perfluoromorpholino group that were produced.
- Abe,Baba,Okuhara,Fukaya
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p. 115 - 128
(2007/10/03)
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- SOLVOLYSIS OF 1-CHLORO-1-ALKENYL PHENYL SULFIDES. SYNTHESIS OF α-BROMO PHENYL THIOCARBOXYLIC ESTERS, α-BROMO ALKYL CARBOXYLIC ESTERS AND α-PHENYLTHIO METHYL CARBOXYLIC ESTERS
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1-Chloro-1-alkenyl phenyl sulfides treated with bromine followed by hydrolysis or methanolysis give α-bromo phenyl thiocarboxylic esters and α-phenylthio methyl carboxylic esters.Direct oxidative solvolysis with bromine and alcohol give α-bromo alkyl carboxylic esters.
- Fortes, C. C.,Chaves, M. H.
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p. 751 - 762
(2007/10/02)
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- Synthesis of α-Phenylthio Enones and Esters of α-Phenylthio Alkenoic Acids
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The title compounds can be made by a Pummerer dehydration from the corresponding saturated sulphoxides.The alkylation of anions from saturated and unsaturated ketones is described.
- Durman, John,Grayson, J.Ian,Hunt, Paul G.,Warren, Stuart
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p. 1939 - 1946
(2007/10/02)
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- ACYLATION OF EXTENDED ENOLATE IONS FROM α-PHENYLTHIO(PhS-)CROTONATE ESTERS
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C-Acylation, like alkylation, occurs at the α-position of title compounds to give unsaturated keto-esters from which the PhS group may be removed.
- Durman, John,Warren, Stuart
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p. 2895 - 2898
(2007/10/02)
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- ALKYLATION OF EXTENDED ENOLATES FROM α-PHENYLTHIO CROTONATE ESTERS
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Conditions are described for the formation of enolate anions from substituted α-phenylthio-crotonate esters and their alkylation at the α-carbon atom.
- Durman, John,Hunt, Paul G.,Warren, Stuart
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p. 2113 - 2116
(2007/10/02)
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