Document Type


Date of Award


Degree Name

Master of Science in Engineering Science- (M.S.)


Chemical Engineering and Chemistry

First Advisor

Richard B. Trattner

Second Advisor

Howard S. Kimmel

Third Advisor

Angelo J. Perna


A review of the decomposition of alkyl and aryl azides by thermolysis and photolysis has been accomplished. Organic azides are a very distinct species that undergo its own unique reactions. Azides decompose to form an electron deficient nitrogen having a sextet of elcctrons. This is called a Nitrene. Nitrenes can exist in the singlet or triplet state. The triplet behaves like a diradical. General and specific reactions of nitrenes have been shown with detailed mechanisms accounting for the products. The main modes of nitrene stabilization are rearrangement, hydrogen abstraction and insertion. Insertion is characteristic of singlet species and abstraction characteristic of the triplet. Some reaction mechanisms during decomposition are concerted while others occur via a stepwise process. Bond reorganization is another method of stabilization (although less common) and is usually limited to aryl compounds. Often, azepines ( a ring enlarged nitrogen compound) is the result of this reoraani-zation. Such reactions occur in the thermolysis or photolysis of pheny azides in amines.



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