77341-90-3Relevant academic research and scientific papers
Applications of allylsamarium bromide as a grignard reagent and a singleelectron transfer reagent in the one-pot synthesis of dienes and trienes
Hu, Yuanyuan,Zhao, Tao,Zhang, Songlin
supporting information; experimental part, p. 1697 - 1705 (2010/06/17)
The utility of allylsamarium bromide, both as a nucleophilic reagent and a single-electron transfer (SET) reagent in the reaction of α-halo, γ-halo-αβ-unsaturated ketones and esters with allylsamarium bromide is reported for the first time in this paper. From a synthetic point of view, a general, efficient and experimentally simple one-pot method for the preparation of 1,4-dienes and trienes is developed. A possible mechanism of the transformation is proposed.
Synthesis of trisubstituted and tetrasubstituted alkenes via a manganate-induced migration-elimination process
Kakiya, Hirotada,Shinokubo, Hiroshi,Oshima, Koichiro
, p. 10063 - 10069 (2007/10/03)
Preparation of alkenes via a manganate-induced alkylation-elimination sequence was investigated. The reaction of 2-alkoxy-1,1-dibromoalkanes with trialkylmanganates afforded disubstituted or trisubstituted alkenes. Treatment of 2-alkoxy-1,1,1-tribromoalkanes with trialkylmanganates provided trisubstituted or tetrasubstituted alkenes through bromine-metal exchange, transfer of two alkyl groups from manganese to carbon, and successive elimination of metal and the β-alkoxy moieties.
Direct and Regioselective Transformation of α-Chloro Carbonyl Compounds into Alkenes and Deuterioalkenes
Barluenga, Jose,Yus, Miguel,Concellon, Jose M.,Bernad, Pablo
, p. 2721 - 2726 (2007/10/02)
The successive treatment ethyl chloroacetate or chloroacetyl chloride with Grignard reagents and lithium powder leads to symmetrical terminal olefins in a regioselective manner.The best results are obtained with acid chlorides.The influence of the temperature and the reaction time on overall yield of the process are studied; in general, yields are increased by working at low temperature (-60 deg C).Internally substituted olefins are obtained from α-chloro acid chlorides through a similar process.The treatment of α-chloro aldehydes, ketones and carboxylic acid derivatives (esters or acid chlorides) with lithium aluminium hydride or lithium aluminium hydride/aluminium chloride and lithium powder at low temperature (-60 deg C) leads in a regioselective manner to olefins with the same carbon skeleton as the starting carbonyl compound.Reactions with lithium aluminium deuteride lead to incorporation of deuterium at predetermined positions in the alkene.
