Max in Graduate School

Here is a picture of Max holding up a bottle of Tetramethylethylenediamine (TMEDA), a very smelly liquid that was the subject of his dissertation at Cornell. TMEDA is a bidentate amine ligand often added to metallations to increase the rate of reaction. The odd thing is that as a ligand TMEDA sucks; It can't even compete with garden variety etherial solvents like THF. Want to know more ? Check these out:

"Polydentate Amine and Ether Solvates of of Lithium Hexamethyldisilazide (LiHMDS): Relationship of Ligand Structure, Relative Solvation Energy, and Aggregation State.", Brett L Lucht, Max P. Bernstein, Julius F. Remenar, and Dr. David Collum, , J. Amer. Chem. Soc. 118, 10707 (1996).

"Solvent and Substrate-Dependent Rates of Imine Metalations by Lithium Diisopropylamide: Understanding the Mechanisms Underlying Krel", Max P. Bernstein and David B. Collum, J. Amer. Chem. Soc. 115, 8008 (1993).

"On the Structure of Lithium Hexamethyldisilazide (LiHMDS) in the Presence of Hexamethylphosphoramide (HMPA). Spectroscopic and Computational Studies of Monomers, Dimers, and Triple Ions", Floyd E. Romesberg, Max P. Bernstein, James H. Gilchrist, David J. Fuller, Aidan T. Harrison, and David B. Collum, J. Amer. Chem. Soc. 115, 3475 (1993).

"Metalation of Imines by Lithium Diisopropylamide Solvation by N,N,N',N'-Tetramethylethylene diamine: Evidence for Solvent-Free Open Dimer Reactive Intermediates", Max P. Bernstein and David B. Collum, J. Amer. Chem. Soc. 115, 789 (1993).

"The Structure and Reactivity of Lithium Diisopropylamide in the Presence of N,N,N,'N' Tetramethylethylenediamine (TMEDA)", Max P. Bernstein, Floyd E. Romesberg, David J. Fuller, Aidan T. Harrison, David B. Collum, Qi-Yong Liu, and Paul G. Willard, J. Amer. Chem. Soc. 114, 5100 (1992).

"On the Structure and Reactivity of Lithium Diisopropylamide in Hydrocarbon Solutions", Yong-Joo Kim, Max P. Bernstein, Angela S. Galiano Roth, Floyd E. Romesberg, Paul G. Willard, David J. Fuller, Aidan T. Harrison, and David B. Collum, Journal of Organic Chemistry, 56, 4435. (1991).

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