Event Title

Generation of Alkynyl Carbenes from Phenanthrene-Based Precursors

Presenter Information

Jamie Suzuki, 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

This work focuses on the generation of alkynyl carbenes from phenanthrene-based precursors. The most common method used to generate carbenes is through the photolysis or pyrolysis of diazo compounds. Although diazo compounds are a proven pathway for carbenes, they are known to be toxic, explosive, and possibly carcinogenic. The two carbenes we hope to study in this thesis are the parent alkynyl carbene and phenylalkynyl carbene. The literature suggests that alkynyl carbenes have not been generated from phenanthrene-based precursors before. The synthesis of the precursor is a four-step process. The carbenes will be generated through photolysis and they will be immediately trapped in 2,3-dimethyl-2-butene. The double bond of 2,3-dimethyl-2-butene will react with the carbene to form a 3-membered ring. These trapped products also be synthesized through a separate route so comparative studies can be performed. A unique characteristic of phenylalkynyl carbene is its ability to resonate. Computational studies will be performed to study the relative stabilities of triplet versus singlet state and the two resonance structures of phenylalkynyl carbene.

Faculty Sponsor

Julie Millard

Sponsoring Department

Colby College. Chemistry Dept.

CLAS Field of Study

Natural Sciences

Event Website

http://www.colby.edu/clas

ID

541

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

Generation of Alkynyl Carbenes from Phenanthrene-Based Precursors

Diamond 145

This work focuses on the generation of alkynyl carbenes from phenanthrene-based precursors. The most common method used to generate carbenes is through the photolysis or pyrolysis of diazo compounds. Although diazo compounds are a proven pathway for carbenes, they are known to be toxic, explosive, and possibly carcinogenic. The two carbenes we hope to study in this thesis are the parent alkynyl carbene and phenylalkynyl carbene. The literature suggests that alkynyl carbenes have not been generated from phenanthrene-based precursors before. The synthesis of the precursor is a four-step process. The carbenes will be generated through photolysis and they will be immediately trapped in 2,3-dimethyl-2-butene. The double bond of 2,3-dimethyl-2-butene will react with the carbene to form a 3-membered ring. These trapped products also be synthesized through a separate route so comparative studies can be performed. A unique characteristic of phenylalkynyl carbene is its ability to resonate. Computational studies will be performed to study the relative stabilities of triplet versus singlet state and the two resonance structures of phenylalkynyl carbene.

http://digitalcommons.colby.edu/clas/2014/program/206