5041-40-7Relevant articles and documents
Iterative synthesis of alkenes by insertion of lithiated epoxides into boronic esters
Bojaryn, Kevin,Fritsch, Stefan,Hirschhaüser, Christoph
supporting information, p. 2218 - 2222 (2019/04/10)
The insertion of lithiated epoxides into boronic esters followed by thermal syn-elimination provides a stereospecific entry to alkenes. This process avoids transition metals and is amenable to iteration to provide higher substitution patterns.
Novel alkylidenating agents of iron(III) derivatives by base-mediated α,μ-dehydrohalogenation and their chemical trapping by cycloaddition
Eisch, John J.,Sohn, Jane U.,Rabinowitz, Edon J.
experimental part, p. 2971 - 2977 (2010/08/20)
Studies of the reactions between group 4 metal, chlorides (M = Ti, Zr, Hf) and methyllithium at -78 °C in toluene can lead to methylidene-metal complexes, H2C=MCl2, by a sequence of monomethylation, α-carbon lithiation and α,μ-elimination of LiCl. Here study of the preparation of alkylidene derivatives of iron was attempted by the interaction of FeCl3 with n-butyllithium in various ratios at -78 °C. The presence of any resulting butylidene-iron(III) derivative, nPrCH=FeE (E = Cl, nBu), was probed by adding chemical trapping agents, such as diphenylacetylene, benzonitrile, methyl benzoate and benzophenone. In each experiment the hydrolyzed products were consistent with a cycloaddition reaction of nPrCH=FeE with the trapping agent. The products from, di-phenylacetylene and from, benzonitrile with D2O workup are uniquely in accord with such a carbene precursor. A 3:1 ratio of nBuLi/FeCl3 gave the optimal yield of nPrCH=FenBu, ca. 80%, from, the MBu2FeCl precursor. When a 3:1. reaction mixture was simply brought to 25 °C and hydrolyzed, the purple alkylidene-iron complex decomposed completely to iron metal. A study of a 3:1 interaction of PhCH2MgCl and FeCl3 under similar conditions and trapping with diphenylacetylene provided evidence for the formation of PhCH=FeCH2Ph in ca. 40%. These results support; the hope that alkylidene-iron(III) analogs of the Grubbs reagents may be accessible by this process.
The Peterson olefination using the tert-butyldiphenylsilyl group: Stereoselective synthesis of di- and trisubstituted alkenes
Barbero,Blanco,Garcia,Pulido
, p. 1223 - 1228 (2007/10/03)
The reaction of α-tert-butyldiphenylsilyl carbonyl compounds with organometallics leads with a high diastereoselectivity to erythro-β-hydroxysilanes, which under acidic or basic elimination conditions give E or Z di- and trisubstituted alkenes.