Presenter Information

Tyler White, Colby CollegeFollow

Location

Lovejoy 215

Start Date

1-5-2014 9:00 AM

End Date

1-5-2014 10:30 AM

Project Type

Presentation

Description

The function of an alkyne as an electron-withdrawing group (EWG) in nucleophilic aromatic substitution (SnAr) reactions has been established by the Katz lab during the past few years. The function of EWGs in SnAr to form macrocyclic organic molecules with oxygen linkers between aromatic carbon systems called oxacalixarenes has been the long-standing interest of the Katz lab. To better understand the way the acetylene group can be used as a modifying substituent in aromatic systems, the homo-coupling of aryl acetylene groups has been explored. This research was followed with subsequent investigation into the resulting diyne functional group as a sufficiently withdrawing group to enable SnAr at the site of the lighter halogens F or Cl with bases containing oxygen or nitrogen with hydrogens or simple organic compounds attached. When substituted into the ortho position, each of the newly substituted group (containing O or N) are then capable of using one of the acetylenes triple bonds to cyclize and form a 2, 2 bis-indole.

Faculty Sponsor

Suzi Cole

Sponsoring Department

Colby College. Chemistry Dept.

CLAS Field of Study

Natural Sciences

Event Website

http://www.colby.edu/clas

ID

691

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May 1st, 9:00 AM May 1st, 10:30 AM

Aryl Alkyne Dimerization and Subsequent SnAr Reactions

Lovejoy 215

The function of an alkyne as an electron-withdrawing group (EWG) in nucleophilic aromatic substitution (SnAr) reactions has been established by the Katz lab during the past few years. The function of EWGs in SnAr to form macrocyclic organic molecules with oxygen linkers between aromatic carbon systems called oxacalixarenes has been the long-standing interest of the Katz lab. To better understand the way the acetylene group can be used as a modifying substituent in aromatic systems, the homo-coupling of aryl acetylene groups has been explored. This research was followed with subsequent investigation into the resulting diyne functional group as a sufficiently withdrawing group to enable SnAr at the site of the lighter halogens F or Cl with bases containing oxygen or nitrogen with hydrogens or simple organic compounds attached. When substituted into the ortho position, each of the newly substituted group (containing O or N) are then capable of using one of the acetylenes triple bonds to cyclize and form a 2, 2 bis-indole.

http://digitalcommons.colby.edu/clas/2014/program/391