39615-80-0Relevant academic research and scientific papers
Catalytic C-H activation of phenylethylamines or benzylamines and their annulation with allenes
Rodrguez, Aleix,Albert, Joan,Ariza, Xavier,Garcia, Jordi,Granell, Jaume,Farrs, Jaume,La Mela, Andrea,Nicols, Ernesto
, p. 9578 - 9585 (2015/02/19)
Tetrahydro-3-benzazepines and tetrahydroisoquinolines are synthesized in one step from allenes and phenylethylamines or benzylamines, respectively. Mechanistically, it is assumed that activation of a C-H bond of an aromatic ring with Pd(II) occurs, directed by the primary amine, leading to the formation of a palladacycle into which an allene then undergoes insertion. The resulting π-allyl intermediate cyclizes to the products by an intramolecular allylic alkylation. The process is particularly useful with 2,3-butadienoates and amines having a quaternary carbon at the α-position. (Chemical Equation Presented).
Nitroalkenes as carbonyl surrogates in arylmethyl-homoallylic alcohol forming one-pot allylation reactions in water
Lin, Mei-Huey,Lin, Wei-Cheng,Liu, Han-Jun,Chuang, Tsung-Hsun
, p. 1278 - 1282 (2013/03/28)
A simple and practical approach has been developed for conducting direct, homoallylic alcohol forming allylation reactions of nitroalkenes in water. Employing the new method, various arylmethyl-homoallylic alcohols can be produced from the corresponding, readily prepared β-nitrostyrenes.
Intramolecular meta photocycloaddition of conformationally restrained 5-phenylpent-1-enes. Part II: Steric and electronic effects caused by 4-mono- and 4-disubstitution
Barentsen, Helma M.,Sieval, Alex B.,Cornelisse, Jan
, p. 7495 - 7520 (2007/10/02)
The meta photocycloaddition of 4-substituted 5-phenylpent-1-enes. 10-18, has been studied. The monosubstituted derivatives always prefer 2,6 addition, independent of the size of the substituent. For 2,6 addition two basic conformations are possible. Disubstituted compounds yield predominantly 1,3 addition with the sterically more demanding group exo. Except for the methoxymethyl and THF derivative the oxygen is found exo as a result of repulsion, while the monohydroxy derivative gives also endo which might be explained by hydrogen bonding. The products from compound 11 change from mainly endo-OH in cyclohexane to chiefly exo-OH in methanol. Much similarity is found with Diels-Alder cycloaddition.
Fluorodestannylation. A Powerful Technique to Liberate Anions of Oxygen, Sulfur, Selenium, and Carbon
Harpp, David N.,Gingras, Marc
, p. 7737 - 7745 (2007/10/02)
Fluoride ions smoothly destannylate organotin chalcogenides to liberate nucleophilic chalcogenide ions; hence the first nucleophilic oxide (O2-) and selenide (Se2-) transfer agents are reported where the tin atom serves as "group 16 (VIB) transfer agent".In the presence of crown ethers or ammonium salts, this process results in a new way to generate "naked" nucleophiles.Ethers and selenides are formed in good to excellent yield.In addition, a useful C-C bond-forming reaction has been developed by using alkyltins with aldehydes and acid chlorides in the presence of fluroide ion.Aspects concerning reactivity and mechanism are presented.Finally, the generality of the fluorodestannylation procedure and the differences with parallel silicon chemistry are detailed.
REACTIVITE DU TETRAALLYLETAIN ET D'ALLYLTRIALKYLETAINS VIS A VIS D'ALDEHYDES, DE CETONES ET D'EPOXYDES
Daude, Gerard,Pereyre, Michel
, p. 43 - 52 (2007/10/02)
Tetraallyltin reacts readily with non activated ketones and exothermically with aldehydes contrary to other allylic organotins such as allyltributyltin.Homoallylic alcohols are obtained after acidolysis of the adducts.Upon extended heating, allylic organotins and epoxides form products which correspond to addition products of isomeric carbonyl compounds.However, starting from cis- and trans-1-phenyl-1,2-epoxypropanes, direct regiospecific but non-stereospecific ring opening is observed with poor yields.
