Carbonyl oxide chemistry. The NIH shift

Biotransformation study of para-substituted phenylpiperazines in Beagle dogs by gas chromatography-mass spectrometry

“…Since then, other authors have tested para-chlorinated and para-methylated derivatives such as fenclocic acid (Foulkes 1970), 1,4-dimethylbenzene oxide (Yagi et al 1972), para-methylanisole (Dunges 1973, Sakurai et al 1982), 4-chloroamphetamine (Parli and Schmidt 1975, para-xylene and 1 -chloronaphthalene (Kumar and Murray 1984), 3,3',4,4'-tetrachlorobiphenyl (Klasson-Wehler et al 1989). This confirmed previous work and, in particular, the ability of these substituents (C1 or CH,) to migrate to the meta-position after para-hydroxylation.…”

“…A shift of this kind, the so-called 'NIH shift', has previously been described (Daly et al 1968 a, b) for para-halogenated and para-methylated derivatives of aniline and acetanilide, since when many other examples of this reaction have been reported (Foulkes 1970, Yagi et al 1972, Dunges 1973, Parli and Schmidt 1975, Sakurai et al 1982, Kumar and Murray 1984, Klasson-Wehler et al 1989.…”

Aromatic Polyazines by a Copper‐Amine Catalyzed Oxidative Polymerization Reaction

“…]-undecene-7, (DBU), benzophenoneimine, aminodiphenylmethane, 1,4-dicyanobenzene, benzoyl chloride, diphenyl ether, all from Aldrich, were used as received or as otherwise stated. Benzophenone hydrazone, [23,24] 4,4 0 -oxybis(benzonitrile) (1b) [25] bis(4-cyanophenyl)sulfide [26] (1c), 1,1 0 -bis(4-benzoylphenyl)ether [27] (4a), 4,4 0 -dibenzoyldiphenyl ether dihydrazone [28] (4b) were synthesized as reported in the literature. Phenyllithium was prepared from bromobenzene as described [29] and used as the ether solution.…”

Arene dioxides of substituted pyrenes: synthesis and X-ray structural studies

“…was used as an internal reference. The multiplicities of the 13 C NMR signals were determined by the attached proton test (APT) pulse sequence. Where necessary, COSY and HETCOR experiments were performed on a Bruker ARX-500 spectrometer ( 1 H, 500.13 MHz; 13 C, 125.76 MHz).…”

“…The multiplicities of the 13 C NMR signals were determined by the attached proton test (APT) pulse sequence. Where necessary, COSY and HETCOR experiments were performed on a Bruker ARX-500 spectrometer ( 1 H, 500.13 MHz; 13 C, 125.76 MHz). Electron impact and chemical ionization mass spectra were recorded, at 70 eV ionizing voltage, on a Hewlett-Packard 5988A twin EI and CI quadrupole mass spectrometer connected to a Hewlett-Packard 5890A gas chromatograph fitted with a Hewlett-Packard 12 mϫ0.2 mmϫ0.33 µm Ultra-1 (cross-linked methyl silicone) column.…”