Abstract:
Abstract
This thesis is divided into two parts. Part one presents a novel method for the synthesis of
naphthalenes bearing aryl substituents. The novel route starts from three simple and
readily available tetralones, α-tetralone, 6-methoxy-α-tetralone and 6,7-dimethoxy-α-
tetralone. By means of standard Suzuki coupling methodology and aromatization
methods, twelve aryl-substituted naphthalenes were synthesized from the tetralones over
five steps in good yields. Some of the aryl-substituted naphthalenes synthesized have
shown positive results when tested against malignant cancer cells. Part one also explains
how unexpected cyclopropa[a]naphthalenes were obtained from 1-aryl-3,4-dihydro-2-
naphthaldehydes by treatment with lithium aluminium hydride.
The methodology developed in part one is further explored in part two of the thesis,
which describes the synthesis of analogues of [1,1’]binaphthalenyl-2,2’-diol. A small
library of twelve different biaryl diols was prepared from simple
bromo(methoxy)naphthaldehydes that were synthesized in part one. The resultant biaryl
diols were used in the design of twenty-two novel phosphite, phosphate, phosphoramidite
and phosphoramidate ligands in which the phosphorus atoms are contained in either a
nine-or an eight-membered heteroatom ring. However, these ligands are still to be tested
in metal-catalyzed hydrogenation reactions.
