title: Synthesis of Esters by in Situ Formation and Trapping of Diazoalkanes.
abstract: A general method has been developed for the in situ formation and trapping of diazoalkanes by carboxylic acids to form esters. The method is applicable to a large variety of carboxylic acids using diazo compounds that are formed from the hydrazones of benzaldehydes and aryl ketones. In situ reaction monitoring with IR spectroscopy (ReactIR) was used to demonstrate that slow addition of the hydrazone to a mixture of oxidant and carboxylic acid avoids the buildup of the diazo compound. This method enables the safe preparation of esters from simple precursors without isolation of diazo compounds.
authors.affiliation: Department of Chemistry, University of California , One Shields Avenue, Davis, California 95616, United States.
authors.forename: Richard A
authors.initials: RA
authors.lastname: Squitieri
authors.affiliation: Department of Chemistry, University of California , One Shields Avenue, Davis, California 95616, United States.
authors.forename: Galen P
authors.initials: GP
authors.lastname: Shearn-Nance
authors.affiliation: Department of Chemistry, University of British Columbia , Vancouver, British Columbia V6T 1Z1, Canada.
authors.forename: Jason E
authors.initials: JE
authors.lastname: Hein
authors.affiliation: Department of Chemistry, University of California , One Shields Avenue, Davis, California 95616, United States.
authors.forename: Jared T
authors.initials: JT
authors.lastname: Shaw