Date of Award

Spring 1991

Document Type

Thesis

Degree Name

Master of Science (MS)

Department

Chemistry & Biochemistry

Program/Concentration

Chemistry

Committee Director

Roy L. Williams

Committee Member

Frank E. Scully, Jr.

Committee Member

Robert L. Ake

Call Number for Print

Special Collections LD4331.C45D67

Abstract

Following a classical synthesis of PCP2 Williams attempted to prepare l,4-diphenyl-1,4-dipiperidino cyclohexane 41 . This approach involved the preparation of 1,4- dicyano-1,4-dipiperidinocyclohexane 7 and the subsequent decyanation of the compound with phenylmagnesium bromide to produce 4. This attempt failed, however, as only the monophenylated product, 8, was thought to be obtained. This product had unique reactivity, producing a blue intermediate upon treatment with halogen in both aqueous and non aqueous media. The same intermediate was produced upon irradiation of a chloroform solution of this product with sunlight or UV light in a UV chamber, with the difference that this reaction produced a solid product upon further irradiation.

In this research, the structural assignment of 8 was reevaluated using NMR, IR, and GC mass spectroscopy, and what was initially thought of as !! was found to be p-dipiperidinobenzene 1.This new structural assignment can now explain the reactivity of 1 towards halogens and light, as it produces a Wurster's dye (a stable radical cation) which is a reaction typical of N,N'-substituted p-phenylenediamines like 1. The solid product produced by the sunlight (or UV light) irradiation of a chloroform solution of 1, was also identified as the hydrochloride of 1. This was due to the fact that chloroform upon irradiation with UV light evolves gaseous hydrogen chloride.

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DOI

10.25777/r50g-dk38

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