The most significant mass spectral features of 14 title compounds are discnssed with the aid of deuterinm labelling experiments. The decomposition patterns of these compounds are strongly &ected by several competing ortho effects, due to the interaction of the nitro fnnction(s) with neighbouring electron-poor N-heterocycles. Very intense polycyclic ions are produced via addition-elimination reactions by loss of simple radicals (H, OH, NO2') from the molecular ion, followed by the ejection of neutral molecules (HN02, CHaCN or CHJVCS). In addition, primary or secondary intramolecular oxygen transfers, preceded or not by hydrogen migration, from the nitro group to the imino carbon via spirocyclic intermediates, are generally observed. Minor skeletal rearrangements, triggered by single or multiple intramolecular oxygen transfer to the bridgehead sulphur atom, followed by SO or SO2 ejection, are also noticed.
The general fragmentation patterns of five selected title compounds are described. The most significant mass spectral features arise from the interaction of aryl substituents with the adjacent heterocyclic ring. The decomposition of the compounds bearing an ortho nitro group in the S‐aryl moieties is strongly affected by a prominent “ortho effect”.
Die Umsetzung der bifunktionellen Alkylierungsmittel (I), (IV), (VII), (IX), (XI), (XIII) und (XV) mit dem Mononatriumsalz des Tosylamids (II) führt in einer Eintopfreaktion zu den 1:1‐Cyclisierungsprodukten (III), (V), (VIII) und (XVI) bzw. zu den 2 : 2‐Produkten (VI), (X), (XII) und (XIV).
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