Date of Award

Fall 1959

Degree Type

Thesis - Restricted

Degree Name

Master of Science (MS)

Department

Chemistry

Abstract

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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