Work

Relative Rates of Transesterification vis-à-vis Newman’s Rule of Six

Year: 2024

Type: article

Abstract: The relative reactivity of a systematic series of simple aliphatic acetate esters has been measured. Exposure of pairs of esters of increasing remote steric hindrance (by altering the degree of branching of the ester alkyl group) to a methanolic solution of Cs 2 CO 3 proved to be a reliable (and general) method for quantitating the rate differences in these base-catalyzed transesterification reactions. The trends in relative rates are in accordance with the qualitative “Rule of Six” put forward by Melvin S. Newman in 1950, as deduced then from interpretation of earlier reports of ease of Fischer esterification reactions.

Source: The Journal of Organic Chemistry

DOI: 10.1021/acs.joc.4c01673

Authors: Arianna M. H. Wheeler, Sei-Chang Ahn, Niklas Kraemer, Thomas R. Hoye

Institution: University of Minnesota

Language: English

Topic: Chemical Reaction Mechanisms

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: National Science Foundation, University of Minnesota, National Institutes of Health, Division of Chemistry

Awards: MRI: Acquisition of a MALDI-TOF/TOF Mass Spectrometer for Molecular Structure Determination and Imaging, G2707391559, Hexadehydro-Diels-Alder (HDDA) Reaction-Enabled Synthesis of Structurally Elaborate, Polycyclic Aromatic Compounds, Upgrade of a 500 MHz NMR Spectrometer for Applications in Biomedical Research, G8928599955