9-Alkyl acridines, formation

Such polycyclic aromatic hydrocarbons as anthracene or heteroaromatics as acridine, phenazine and 2,4,5-triphenyl oxazole act as Jt-donors for the Jt-acceptors AN and alkyl methacrylates [50-53]. Again, the interaction of the donor excited states with vinyl monomers leads to exciplex formation. But, the rate constants (k ) of these quenching processess are low compared to other quenching reactions (see Table 1). The assumed electron transfer character is supported by the influence of the donor reduction potential on the k value (see Table 1), and the detection of the monomer cation radicals with the anthracene-MMA system. Then, the ion radicals initiate the polymerization, the detailed mechanism of which is unsolved,... 

On the subject of spontaneous generation of chirality, it is of interest to know that spontaneous formation of chiral aggregates from nonchiral monomers is known to occur, e.g. the assembly of tetra-alkyl benzimidocyanins 3 as monitored by CD (circular dichroism). Formation of chiral crystals from achiral monomers is also reported, e.g. by photodimerization in the solid state. " In a recent example, chiral crystals of acridine 4 and diphenylacetic acid 5 give excess of the (.S)-product 6 upon a photodecarboxylating condensation reaction. Symmetry breaking is also known to occur for supramolecular complexes of achiral components e.g. glu-tarimide 7 and the diaminopyridine 8, and, as will be discussed below, in monolayers at the air-water interface. ... 

Many analogs of nucleic and folic adds, which interfere with DNA synthesis, can be expected to cause chromosomal breaks. Similarly, breaks are caused by substances that alkylate DNA, such as bifunctional mitomycin C— which causes the formation of interstrand breaks—or the monofunctional streptronigrin, actinomydn, and neomycin— which form covalent bonds with DNA strands and intercalate between the strands (see Necrosis). Photodynamic dyes, like acridine or its derivative quinacrine, intercalate between DNA strands and in the presence of light and oxygen cause the strands to break. The fungicides Captan and maleic hydrazide (used to retard growth of ivy and grass) cause chromosomal breaks in vitro. 

The acridine-based PNP pincer complex 16 catalyzes the selective formation of primary amines [73] directly from alcohols and ammonia (Table 6). Among the amines, the terminal primary amines are the most useful, but in general then-selective synthesis is challenging. Primary amines are more nucleophilic than ammonia and compete with it in reaction with electrophiles such as alkyl halides or aldehydes, producing secondary amines, which can also react, leading to the formation of mixtures of products. 

Apart from alkylations and arylation of NIO of acridine, the formation of N—B bonds is possible. A borenium cation 184 was formed on addition of aluminum chloride to the acridine—trichloroborane adduct 183 formed under the conditions shown in Scheme 72 (2013OM6712). Depending on the conditions, different products were obtained. 

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