Date of Award
Thesis - Restricted
Master of Science (MS)
The deaminatlon of primary aliphatic amines, alicyclic and acyclic, with nitrous acid is not as simple as many textbooks imply. In fact, a completely satisfactory elucidation of the mechanism of this reaction has not been proposed as yet . When the amino group is attached to a ring system such as the very interesting pinane skeleton, the problem is further complicated by still other phenomena such as the Demjanov and Wagner-Meerwein rearrangements. The molecule chosen for study was 2-aminoapopinane, of which there is little mention in the chemical literature. Hence the problem was twofold: synthesis of the desired terpenic amine and deamination with emphasis on identifying the products. It is hoped that a knowledge of the deamination products will help to explain a little more about the reaction mechanism of nitrous acid deaminations.
Ratajczyk, James Daniel, "The Preparation and Deamination of Cis-2-Aminoapopinane" (1959). Master's Theses (1922-2009) Access restricted to Marquette Campus. 2682.