Stereochemistry of the Allene-Forming Cycloelimination of 4-Diazo-3,5-Diethyl-3,5-Dimethyl-1-Pyrazoline

The goal of this investigation was the determination of the stereochemical course of the decomposition of diazopyrazoline 1a to 3,5-dimethyl-3,4-heptadiene (2). To achieve this goal, a stereospecific synthesis of 1a which would permit its optical resolution was devised. Cyclization of tosylhydrazine and 4,5-epoxy-5-methyl-3-heptanone (3) provides a mixture of diastereomeric pyrazolols 4a and 5a, which upon oxidation to the

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

2014

Author dc:creator

• Hoover, Dennis Jay

• Chemistry, Organic

Language dc:language

eng

Identifier

(UMI)AAI8108543

OAI identifier oai:identifier

oai:www.ideals.illinois.edu:2142/67242