3330-05-0Relevant academic research and scientific papers
Three-component coupling reactions of thioformamides with organolithium and grignard reagents leading to formation of tertiary amines and a thiolating agent
Murai, Toshiaki,Asai, Fumio
, p. 780 - 781 (2007/10/03)
A highly efficient three-component coupling reaction between thioformamides and organolithium and Grignard reagents was developed. The generality of the process has been demonstrated by using various combinations of reactants and reagents. Information about the mechanism of the reaction has come from 1H and 13C NMR spectroscopic detection of the key intermediate. The LiS group in the intermediates generated by addition of the organolithium reagents to the thioformamides serves as a leaving group. The solid byproduct formed in these reactions, formulated as [LiSMgBr], can be used as a thiolating agent to transform acid chlorides into thioic acids and thioic acid anhydrides. Copyright
TERTIARY AMINE AND METHOD FOR PRODUCING THE SAME
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Page/Page column 21, (2010/02/10)
PROBLEM TO BE SOLVED: To provide a new tertiary amine and a method for easily producing the tertiary amine in improved yield. SOLUTION: The tertiary amine is expressed by general formula (1) and produced by adding a thioamide expressed by general formula
Tertiary amine and method for producing the same
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Page 10, (2010/02/09)
The present invention relates to a method for easily producing a tertiary amine with high yield. A tertiary amine represented by general formula (1) is produced by adding a metal-containing reagent represented by general formula (6) into a reaction system
Metallation of benzylic amines via amine-borane complexes
Ebden, Mark R.,Simpkins, Nigel S.,Fox, David N.A.
, p. 12923 - 12952 (2007/10/03)
Formation of borane complexes of N,N-dimethylbenzylamine, N,N- dimethyl(1-naphthyl)methylamine, N,N-dimethyl(2-naphthyl)methylamine, N- methyltetrahydroisoquinoline and N-methylisoindoline facilitates regioselective metallation of these systems using BuLi, giving intermediate benzylic anions which react with a range of electrophiles to give products in good yield.
Activation of Benzylic Amines Towards Regioselective Metallation by Borane Complex Formation
Ebden, Mark R.,Simpkins, Nigel S.,Fox, David N. A.
, p. 8697 - 8700 (2007/10/02)
Formation of borane complexes of N,N-dimethylbenzylamine 4 and N-methyltetrahydroisoquinoline 1 facilitates regioselective metallation of these systems using BuLi, giving benzylic anions which react with a range of electrophiles.
THE EFFECT OF PHENYL SUBSTITUENTS ON ELIMINATION STEREOCHEMISTRY: A MECHANISTIC MANIFOLD IN ALKOXIDE PROMOTED DECOMPOSITION OF 1-PHENYL-1-PROPYLTRIMETHYLAMMONIUM ION
Machkova, Zuzana,Zavada, Jiri
, p. 833 - 849 (2007/10/02)
Reactions of the positionally isomeric 1-phenyl-1-propyl (I) and 1-phenyl-2-propyltrimethylammonium (II) ions with CH3OK - CH3OH, t-C4H9OK - t-C4H9OH and t-C4H9OK - C6H6 systems have been investigated with aid of the deuterated analogues erythro-2-D-I, threo-2-D-I, 1-D-I and threo-1-D-II.At least five mechanistic components (anti-β-elimination, syn-β-elimination, α',β-elimination, Sommelet-Hauser rearrangement and SN2 substitution) have been found to participate in the reaction of the quaternary compound I, in proportions varying greatly with base-solvent combination.The corresponding reactions of the isomeric compound II proceeded in a more simple manner, withount the intervention of ylide pathways in the olefin as well as in the amine formation.The stereochemistry of β-elimination determined for the two phenyl-substituted 'onium compounds has been compared with that reported previously for structurally related aliphatic analogues.The "anomalously" low propensity for syn-elimination as well as the "anomalously" high values of trans/cis-olefin rations in anti-elimination stigmatizing the presence of phenyl substituents are proposed to originate from a lack of base-approach hindrance in the reaction.
