10.1111/j.2042-7158.1974.tb09281.x
The research investigates the structure of nitrones derived from amphetamines, specifically focusing on the major in vitro metabolic product of fenfluramine. Initially, the authors identified the major metabolic product as a nitrone, deducing its structure based on its reduction to N-hydroxyfenfluramine and subsequent regeneration using lithium aluminium hydride and yellow mercuric oxide. They initially proposed structure IIa for this nitrone but later revised it to IIIa after further studies and mass spectral evidence suggested that structures IIa and IIIa could not be differentiated by mass spectral data alone. The authors used various chemicals in their research, including N-hydroxy-N-n-propylamphetamine, N-ethyl-N-hydroxyamphetamine, yellow mercuric oxide, lithium aluminium hydride, and m-chloroperbenzoic acid. They also employed techniques such as gas chromatography, nuclear magnetic resonance (NMR) spectroscopy, and mass spectrometry to analyze and confirm the structures of the nitrones. The study ultimately concluded that nitrones of general structure III are the major and likely exclusive initial products of mild oxidation of N-alkyl-N-hydroxyamphetamines, and these nitrones are more stable than previously suggested.
10.1021/ja00721a042
The research explores a novel method for the introduction of two carbon appendages at a carbonyl carbon, with applications in double chain branching and spiro annulation operations. The study aims to replace carbonyl oxygen with two functionalized carbon substituents that can be further elaborated into rings or more complex chains. The method involves a two-step sequence: first, the formation of allyl enol ethers using ylides, and second, the thermolysis of these enol ethers to yield doubly branched unsaturated aldehydes. Key chemicals used include allyloxymethyltriphenylphosphonium chloride and sec-butyllithium for the formation of ylides, and various carbonyl compounds such as cyclohexanone and benzaldehyde for the branching-annulation sequence. The study also introduces modifications to broaden the scope of the method, such as using diethyl allylthiomethylphosphonate and red mercuric oxide to promote the thio-Claisen rearrangement. The results demonstrate the utility of this method in synthesizing a variety of spiro systems and complex chains, with satisfactory yields and elemental analyses. The research concludes that this two-step sequence is a valuable and flexible approach for the synthesis of complex organic structures.
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