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James J. Kiddle, Ph. D.  -  Microwave Chemistry P-bs.gif (8777 bytes)

Michaelis-Arbuzov Rearrangement - Synthesis of Phosphonates

A diverse series of phosphonate esters have been prepared using a domestic microwave oven. The microwave enhanced Michaelis-Arbuzov reaction shows remarkable rate acceleration under microwave irradiation and allows the facile synthesis, and in certain cases easy workup, of alkyl, -substituted and aryl phosphonates. In addition, the rapid reaction time also reduces the formation of the undesired phosphonate 5.

Wittig Reagents - Synthesis of Phosphonium Salts

Several phosphonium salts have been prepared using a domestic microwave oven. The microwave enhanced reaction of triphenyl phosphine and an organic halide shows a remarkable rate acceleration under microwave irradiation and allows the general and facile synthesis of both stabilized and non-stabilized phosphonium salts.

Scale-up of Microwave Reactions

Representative phosphonates and phosphonium salts have been prepared on a moderate scale (25-50g) using a domestic microwave oven. The reactions, conducted in sealed hydrogenation vessels, showed remarkable rate acceleration and excellent yields (>95%) employing this methodology.

Ring Closing Metathesis Under Microwave Heating

In the past decade ring closing metathesis (RCM) has become an important tool for the construction of carbocyclic ring systems.  The development of well defined, air, and moisture stable ruthenium based catalysts has further expanded the scope of this reaction.  Currently under investigation in our laboratory is the application of rapid microwave heating in RCM reactions.  In conjunction with this project the use of ionic liquids as useful "green solvents" for microwave reactions is also under investigation.


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