PubMed · 13816801
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D DIMITROV, D MULCHANOV. 1960. [Acute naphthalane poisoning].. https://pubmed.ncbi.nlm.nih.gov/13816801/
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A circular dichroism (CD) spectral study on chiral aromatic chain imides possessing anthracene and naphthalene moieties with bulky N substituents showed that their helical chirality based on folding remained for a reasonably long time without racemization in solution. Racemization due to conformational equilibration occurred very slowly, requiring over 1 week at ambient temperature. Their CD spectra both in solution and in the solid state gave similar CD signals, suggesting retention of helicity observed in the solid state even after dissolving. As an application of this novel chiral folding of aromatic chain imides, a chiral photochromic system was investigated based on the photo [4 + 4] cycloaddition and its thermal cycloreversion of an anthracene-naphthalene system. The foldamer possessing an anthracene moiety in the center connected with two naphthalene moieties below and above it by iminodicarbonyl linkers was prepared for this purpose. Induced CD was observed for the foldamer with (S)-1-(1-naphthyl)ethyl substituents at the imide nitrogen atoms. Chiral photochromic cycles were monitored by CD spectral measurement.
Experimental and theoretical B3PW91/6-31G* spectra of diisopropylnaphthalene (DIPN) were compared. For the 1,3- and 2,6-DIPN isomers, which were isolated as pure compounds, the theoretical IR spectra were scaled down and were shown to fit the experimental spectra very well. The same scaling factor was used for comparison theoretical and experimental spectra of isomers present in unresolved mixtures of isomers, i.e. 1,4-, 1,5-, 1,6-, 1,7-, and 2,7-DIPNs. For three isomers, 1,2-, 1,8-, and 2,3-DIPN, the experimental IR spectra, unknown so far, were predicted.
[reaction: see text]. A synthesis of a reduced version of the naphthazarin found in the rubromycin class of natural products is reported. The naphthalene ring system is formed via a Dötz reaction with a symmetrical alkyne. Differentiation between the C1' and C3' groups of the Dötz adduct is achieved by selective oxidation since the two methylene groups possess different oxidation potentials.