Event Title

Towards the Synthesis of a Novel Copper(I) Ethyl-2-Naphthyl Appended 1-aza-4,8-dithiacyclodecane Complex

Presenter Information

Max Cushner, Colby CollegeFollow

Location

Diamond 145

Start Date

1-5-2014 1:00 PM

End Date

1-5-2014 2:30 PM

Project Type

Presentation

Description

Organocopper reagents are among some of the most popular organometallics complexes available for organic synthesis. These organocopper complexes allow for a wide range of stereoselective and regioselective additions onto large molecules in high yield. While there are exhaustive lists of alkyl, alkenyl, and aryl copper(I) complexes, there are only a few copper(I)-arene complexes known. By studying copper(I)-arene complexes, we can further understand the properties and uses of these complexes. The Conry group has previously synthesized a copper(I)-naphthyl complex that can act as a catalyst for the aziridination of olefins. This copper(I)-naphthyl complex exists in the solid-state and in solution, which is unprecedented as other copper(I)-arene complexes only exist in the solid-state. The current project focuses on synthesizing a modified copper(I)-naphthyl complex; the previously reported ligand appended 1-aza-4,8-dithiacyclodecane to naphthlene by an ethyl linking arm at the 1 position of naphthlene. We aim to probe the importance of the placement of the ethyl linking arm by placing the ethyl arm at the 2 position of the naphthlene. This difference in bond position may greatly change the binding strength of the naphthyl group to the copper(I) ion.

Faculty Sponsor

Julie Millard

Sponsoring Department

Colby College. Chemistry Dept.

CLAS Field of Study

Natural Sciences

Event Website

http://www.colby.edu/clas

ID

372

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May 1st, 1:00 PM May 1st, 2:30 PM

Towards the Synthesis of a Novel Copper(I) Ethyl-2-Naphthyl Appended 1-aza-4,8-dithiacyclodecane Complex

Diamond 145

Organocopper reagents are among some of the most popular organometallics complexes available for organic synthesis. These organocopper complexes allow for a wide range of stereoselective and regioselective additions onto large molecules in high yield. While there are exhaustive lists of alkyl, alkenyl, and aryl copper(I) complexes, there are only a few copper(I)-arene complexes known. By studying copper(I)-arene complexes, we can further understand the properties and uses of these complexes. The Conry group has previously synthesized a copper(I)-naphthyl complex that can act as a catalyst for the aziridination of olefins. This copper(I)-naphthyl complex exists in the solid-state and in solution, which is unprecedented as other copper(I)-arene complexes only exist in the solid-state. The current project focuses on synthesizing a modified copper(I)-naphthyl complex; the previously reported ligand appended 1-aza-4,8-dithiacyclodecane to naphthlene by an ethyl linking arm at the 1 position of naphthlene. We aim to probe the importance of the placement of the ethyl linking arm by placing the ethyl arm at the 2 position of the naphthlene. This difference in bond position may greatly change the binding strength of the naphthyl group to the copper(I) ion.

http://digitalcommons.colby.edu/clas/2014/program/284