Literature DB >> 17909502

Unusual reactivity patterns of 1,3,6,8-tetraazatricyclo-[4.4.1.1(3,8)]-dodecane (TATD) towards some reducing agents: synthesis of TMEDA.

Augusto Rivera1, Jaime Rios-Motta.   

Abstract

N,N,N,N-tetramethylethylenediamine (TMEDA) can be synthesized by simple reduction of 1,3,6,8-tetraazatricyclo-[4.4.1.1.(3,8)]dodecane (TATD), an aminal cage type amine, with formic acid. The aminal can be converted to TMEDA in high yield very easily and in a very short time. We comment on the scope and limitations of the reduction of this aminal and propose a possible reaction mechanism.

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Year:  2007        PMID： 17909502      PMCID： PMC6149478          DOI： 10.3390/12071471

Source DB:  PubMed          Journal:  Molecules        ISSN： 1420-3049            Impact factor:   4.411


  16 in total

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Journal:  J Org Chem       Date:  2006-10-13       Impact factor: 4.354

2.  Controlled/"Living" Radical Polymerization of 2-(Dimethylamino)ethyl Methacrylate.

Authors: 
Journal:  Macromolecules       Date:  1998-07-28       Impact factor: 5.985

3.  Coordination polymers of copper(I) halides.

Authors:  P M Graham; R D Pike; M Sabat; R D Bailey; W T Pennington
Journal:  Inorg Chem       Date:  2000-10-30       Impact factor: 5.165

4.  Electron and nuclear positions in the short hydrogen bond in urotropine-N-oxide.formic acid.

Authors:  Cara L Nygren; Chick C Wilson; John F C Turner
Journal:  J Phys Chem A       Date:  2005-03-10       Impact factor: 2.781

5.  Consequences of correlated solvation on the structures and reactivities of RLi-diamine complexes: 1,2-addition and alpha-lithiation reactions of imines by TMEDA-solvated n-butyllithium and phenyllithium.

Authors:  Jennifer L Rutherford; Daniele Hoffmann; David B Collum
Journal:  J Am Chem Soc       Date:  2002-01-16       Impact factor: 15.419

6.  Directed dihydroxylation of cyclic allylic alcohols and trichloroacetamides using OsO4/TMEDA.

Authors:  Timothy J Donohoe; Kevin Blades; Peter R Moore; Michael J Waring; Jon J G Winter; Madeleine Helliwell; Nicholas J Newcombe; Geoffrey Stemp
Journal:  J Org Chem       Date:  2002-11-15       Impact factor: 4.354

7.  Diamine-catalyzed asymmetric Michael additions of aldehydes and ketones to nitrostyrene.

Authors:  Alexandre Alexakis; Olivier Andrey
Journal:  Org Lett       Date:  2002-10-17       Impact factor: 6.005

8.  Crystal Structures of a Series of Complexes Produced by Reaction of Copper(I) Cyanide with Diamines.

Authors:  Fred B. Stocker; Teodora P. Staeva; Chad M. Rienstra; Doyle Britton
Journal:  Inorg Chem       Date:  1999-03-08       Impact factor: 5.165

9.  Syntheses of two new 1D and 3D networks of Cu(II) and Co(II) using malonate and urotropine as bridging ligands: crystal structures and magnetic studies.

Authors:  Sanjit Konar; Partha Sarathi Mukherjee; Michael G B Drew; Joan Ribas; Nirmalendu Ray Chaudhuri
Journal:  Inorg Chem       Date:  2003-04-21       Impact factor: 5.165

10.  Methods for the synthesis of polyhydroxylated piperidines by diastereoselective dihydroxylation: exploitation in the two-directional synthesis of aza-C-linked disaccharide derivatives.

Authors:  Andrew Kennedy; Adam Nelson; Alexis Perry
Journal:  Beilstein J Org Chem       Date:  2005-08-26       Impact factor: 2.883
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