2- alkanoate alkene

Alkanes, dipurin-8-yl-synthesis, 5, 574 Alkanes, poly-N-pyrazoIyl-synthesis, 5, 320 Alkanoic acids, tetrazolyl-anti-inflammatory activity, 5, 835 Alkanoic acids, 4-thienyi-cyclization, 4, 905-906 Alkene metathesis mechanism, 1, 668 Alkenes activated... 

Faraday, in 1834, was the first to encounter Kolbe-electrolysis, when he studied the electrolysis of an aqueous acetate solution [1], However, it was Kolbe, in 1849, who recognized the reaction and applied it to the synthesis of a number of hydrocarbons [2]. Thereby the name of the reaction originated. Later on Wurtz demonstrated that unsymmetrical coupling products could be prepared by coelectrolysis of two different alkanoates [3]. Difficulties in the coupling of dicarboxylic acids were overcome by Crum-Brown and Walker, when they electrolysed the half esters of the diacids instead [4]. This way a simple route to useful long chain l,n-dicarboxylic acids was developed. In some cases the Kolbe dimerization failed and alkenes, alcohols or esters became the main products. The formation of alcohols by anodic oxidation of carboxylates in water was called the Hofer-Moest reaction [5]. Further applications and limitations were afterwards foimd by Fichter [6]. Weedon extensively applied the Kolbe reaction to the synthesis of rare fatty acids and similar natural products [7]. Later on key features of the mechanism were worked out by Eberson [8] and Utley [9] from the point of view of organic chemists and by Conway [10] from the point of view of a physical chemist. In Germany [11], Russia [12], and Japan [13] Kolbe electrolysis of adipic halfesters has been scaled up to a technical process. 

Chlorinated, Brominated, and Iodinated Alkanes, Alkenes, and Alkanoates... 

A range of mechanisms has been found for the biodegradation of halogenated alkanes, alkenes, and alkanoates ... 

Alkyl alkanoates are reduced only at very negative potentials so that preparative scale experiments at mercury or lead cathodes are not successful. Phenyl alkanoates afford 30-36% yields of the alkan-l-ol under acid conditions [148]. Preparative scale reduction of methyl alkanoates is best achieved at a magnesium cathode in tetrahydrofuran containing tm-butanol as proton donor. The reaction is carried out in an undivided cell with a sacrificial magnesium anode and affords the alkan-l-ol in good yields [151]. In the absence of a proton donor and in the presence of chlorotrimethylsilane, acyloin derivatives 30 arc formed in a process related to the acyloin condensation of esters using sodium in xylene [152], Radical-anions formed initially can be trapped by intramolecular addition to an alkene function in substrates such as 31 to give aiicyclic products [151]. 

Dondoni et al. prepared a 1-hydroxyethylene peptide using a thiazole-aldehyde synthesis starting from an amino acid.[38] The aldehyde is converted into an alkanoate by Wittig alkenation and reduction of the double bond (Scheme 18). Then, removal of the tert-bu-tyldimethylsilyl group gives the unsubstituted lactone. In the last step, the lactone is alkylated using the method reported by Kleinman and co-workers. 20 ... 

Method of Wakita, Yoshlmoto, Miyamoto, and Watanabe The Wakita et al. method [46] has been derived with a set of 307 liquid compounds, including alkanes, alkenes, alkynes, halogenated alkanes, alkanols, oxoalkanes, alkanones, alkyl alkanoates, alkanethiols, alkanenitriles, nitroalkanes, and substituted benzenes, naphthalenes, and biphenyles. The model equation is... 

RC02R (all alkano-lides), 2-alken-l-one, 2-alkenoate ester, 2-alkenenitrile (all 2-cyclopente-nones)... 

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