Solvent Effects on the Rate of Ozonolysis: Development of a Homogeneous Flow Ozonolysis Protocol

Abstract

Herein we describe the effect of organic solvents on ozone solubility and rate of ozonolysis reactions using rapid injection NMR spectroscopy. The tabulated solubility and kinetic data allowed for the design of a homogeneous ozonolysis flow reactor capable of delivering precise quantities of dissolved ozone to various olefin substrates.

Effect of Solvent on the Rate of Ozonolysis: Development of a Homogeneous Flow Ozonolysis Protocol

“…These insights were leveraged in the development of a simple, homogeneous flow protocol for the ozonolysis of various olefin substrates with broad functionality. 25 Mechanistic investigations into ozonolysis reactions have mainly focused on observing and determining the lifetimes of intermediates formed along the reaction pathway such as primary ozonides or Criegee intermediates. 20,26,27 Although substitution patterns about the olefin substrate are well-known to influence reaction rates of ozonolysis, the effect of solvent on these processes remains largely unexplored.…”