Methodology

Our synthesis of synthesize 3,5 disubstituted isoxazoline consisted of the following reactions:

Grignard Reaction: Changes P.Anisaldehyde into 1- (4-Methoxyphenyl)-3-buten-1-ol
Oxidation Reaction: Changes 1-(4-Methoxyphenyl)-3-buten-1-ol into ketone
Oximation Reaction: Changes ketone into oxime
Cyclization Reaction: Changes oxime into 3,5-disubstituted Δ2-isoxazoline

Grignard Reaction

Oxidation Reaction

Oximation Reaction

Cyclization Reaction

This image depicts an oxidation reaction that occurs in the round-bottom flask.

Cyclization Reaction Overview

The cyclization reaction was the final out of four reactions. In this step, the isoxazole ring structure was closed, giving us the final product of 3,5-disubstituted Δ2-isoxazoline.

The metal mediator was varied in different cyclizations.
The amounts of each particular metal mediator were also varied in different cyclizations
We used Nickel (II) Chloride and also Lead (II) Acetate the experimental cyclizations

The image on the left depicts the cyclizations using Lead (II) Acetate and Nickel (II) Chloride (respectively) as the metal mediators.

The image on the right depicts the cyclizations using 5% Nickel (II) Chloride and a 5% Palladium (II) Chloride (respectively) as the metal mediators. In addition both used 300% Copper (II) Chloride as an oxidizing agent