Document Type

Thesis

Degree

Master of Science (MS)

Department

Chemistry

First Advisor's Name

Kevin O'Shea

First Advisor's Committee Title

Committee Chair

Second Advisor's Name

Rudolf Jaffe

Third Advisor's Name

David Becker

Date of Defense

3-29-2006

Abstract

A study of the reaction pathways of 1,1-diphenylethylene; methyleneindan; fluorenene; trans,trans-1,4-diphenyl-1,3-butadiene; cis,trans-1,4-diphenyl-1,3- butadiene and cis,cis-1,4-diphenyl-1,3-butadiene with singlet oxygen and the singlet oxygen mimic, 4-alkyl-1,2,4-triazoline-3,5-dione (RTAD) has been undertaken. Comparisons of the reactivity and reaction mechanisms among the isomers and electrophiles have been conducted. Singlet oxygen exhibits significantly lower reactivity compared to RTAD. RTAD reacts with 1,1- diphenylethylene to produce 4+2/ene and 4+2/4+2 (2:1) adducts but with methyleneindan to give a complex mixture including the ene adduct. Reactions of isomeric 1,4-diphenyl-1,3-butadienes with RTAD produce 4+2 adducts. The results of the studies provide fundamental mechanistic information which is important to a better understanding of the detrimental and beneficial reactions of 1O2 in biological systems and the environment.

Identifier

FI14062201

Comments

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Chemistry Commons

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