Dioxirane-mediated epoxidation of alkenes: The development of catalytic and asymmetric protocols

A practical, general and efficient protocol for the catalytic epoxidation of alkenes has been developed. The in situ generation of reactive dioxiranes capable of epoxidizing a variety of alkenes under biphasic conditions has been accomplished using phase transfer catalysts bearing a carbonyl group. Optimal epoxidation conditions employ 10 mol % of 1-dodecyl-1-methyl-4-oxopiperidinium trifluoromethanesulfonate (9d$\sp+$OTf$\sp-)$ in a $\rm CH\sb2Cl\sb2$/pH $7.5{-}8.0$ biphase using potassium monoperoxosulfate (Oxone) as the oxidant. Optimization of the conditions identified (1) slow addition rate, (2) pH 7.5-8.0, (3) n-dodecyl chain, and (4) the triflate salt as key experimental and structural variables.

Name thesis:degree_name

Ph.D.

Level thesis:degree_level

Dissertation

Discipline thesis:degree_discipline

Chemistry

Grantor

University of Illinois at Urbana-Champaign

Year dc:date

2011

Author dc:creator

• Forbes, David Christopher

Contributors dc:contributor

• Denmark, Scott E.

• Chemistry, Organic

Statement dc:rights

• Copyright 1996 Forbes, David Christopher

Language dc:language

eng

Identifier

9780591087567
AAI9702514
(UMI)AAI9702514

OAI identifier oai:identifier

oai:www.ideals.illinois.edu:2142/19549