The benzannelated dihydropyrenes 3 and 4 were synthesized from l,3-bis(bromomethyl)naphthalene ( 16) and l,3-bis(bromomethyl)-2-methylnaphthalene (22) (the latter obtained in 18% yield in seven steps from 2,3-dimethylnaphthalene) in 7.4% and 4.8% overall yields, respectively, using Stevens or Wittig rearrangement-Hofmann elimination sequences on the dithiacyclophanes 13 and 14, followed by valence tautomerization of the resulting cyclophanedienes 11 and 12. The dihydrobenzopyrene 3 rapidly dehydrogenates to benzo[a]pyrene (21), whereas the dimethyl derivative 4 is relatively stable.
Durch Kondensation des Dibromids (I) mit Bis‐ (mercaptomethyl)‐aromaten wie z.B. (II) in großer Verdünnung entstehen das Dithiacyclophan (III) sowie die Analogen (IV) und (V).
Reaction of DT type pesticides with anisoie and A1Cl3 in CS2 yielded unsym-tetraarylethylenes (Ar2C=Ar2′), which on photocyclisation yielded phenanthrenes. Further oxidative closure to dibenzo[g,p]chrysenes occurs under conditions that faveur cation radical intermediates. Chromatography of commercial methoxychlor (DMDT) yielded tetraanisylethylene together with minor amounts of the corresponding photo products, 3,6-dimethoxy-9,10-dianisylphenanthrene and 3,6,11,14-tetramethoxydibenzo[g,p]chrysene, as well as other chloroanisylethylenes.
Sorgfältige chromatographische Analyse von kommerziellem Methoxychlor (DMDT) (III), das gewöhnlich aus Anisol (I) und Choral (II) hergestellt wird, zeigt die Anweä senheit der Verbindungen (IVa) (TAE), (IVb)(DMDE), (IVc) (Chlortrianisen, Hormonisen, Merbentul) sowie der polycyclischen Aromaten (V) und (VI).
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