Peroxides are often unwanted products formed in the trapping of radicals with molecular oxygen. Radicals are normally highly reactive intermediates that react with most organic molecules and with molecular oxygen, and catalysis for the generation of radicals has been known for decades. A major challenge is controlling such reactions to make useful products that are formed in high yields with high selectivity. The use of peroxides can easily form products in high selectivity and high yields. Our group has developed an addition novel transformation that involves the combination of four essential reagents that include an alkene, tert-butyl hydroperoxide (TBHP), chloroform, and an aliphatic tertiary amine to add the dichloromethyl and tert-butylperoxy radicals across the carbon-carbon double bond of the alkene. These reactions occur in the presence of copper(I) iodide, and do not occur in its absence. Styrene and substituted styrenes give high yields of the addition product which is formed regioselectively so that the tert-butylperoxy group is at the phenyl-substituted carbon. Ongoing mechanistic studies are being performed to determine the mechanism of these reactions.

Synthesis of 1-(1-<i>tert</i>-butylperoxy)-3,3-dichloropropylbenzenes

2019 Spring National Meeting

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.

Synthesis of 1-(1-tert-butylperoxy)-3,3-dichloropropylbenzenes