Date of Award

Fall 1959

Degree Type

Thesis - Restricted

Degree Name

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.



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