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March 25, 2008

Chem Synth Lecture 12/3/08


Classical Radical Cyclisation

lecture 7


Endo vs. exo determined by Baldwin's Rules

Stoichiometric in Bu3SnH, involves loss of functionality, toxic reagents, purification issues (Sn), expensive 

Atom Transfer Cyclisation

lecture 8

30mol% CuCl, MeCN, 140degC (sealed container as above the boiling point of the solvent) 

Allows functional groups in final product, only 30mol% required (better than stoichiometric)

Addition of a ligand (bipy), temperature drops to 110degC, 12 hours

The ligand solubalises the copper

To create a second generation catalyst for use, the synthesis of the catalyst must be simple, and the reaction must be fast and easy

lecture 9

1hour, room temperature

Curiously, solution vs solid support give different stereochemistries 

By moving the double bond by one carbon a Radical Polar Crossover Reaction can be initiated, stabilised by the closer double bond

lecture 10

Where the hydrogen for the formation of the final double bond can come from one of two positions

Other work - Polymer and composite materials from plant matter in renewable plastics manufacture


Work done into Organometallic complexes of Nobel Gases

TM alkane and nobel gas complexes in solution at room temperature

allows NMR work, determination of the activation perameters for the reaction of such transient species with CO

CpRe(CO)2Xe, CpRe(CO)2PF3, CpRe(CO)PF3Xe

By fluoroine NMR

Shows real bond strengths (ie, truely bonded to metal). The covalent Xe bond discovered (by F-Xe coupling) completely outside the known ppm for complexed Xe (-6100ppm) 

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