Explosion bei der Herstellung von Trinitrosophloroglucin

Freund, H. E.

doi:10.1002/ange.19610731205

Angewandte Chemie

1961

DOI: 10.1002/ange.19610731205

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Explosion bei der Herstellung von Trinitrosophloroglucin

H. E. Freund¹

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2017

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Hydroxy‐ and Methoxybenzene Derivatives with Benzenediazonium Salts ― Chemical Behavior and Tautomeric Problems

et al. 2017

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The azo‐coupling reactions between 4‐nitrobenzenediazonium tetrafluoroborate and a series of benzene derivatives bearing at least one electron‐donating hydroxy or methoxy substituent have been studied. Depending on the nucleophile and its relative ratio with the diazonium salt, it was possible to obtain mono‐ and disubstituted products as well as a trisubstituted product for phloroglucinol. The reactions between 3,5‐diaminoanisole or 3,5‐diaminophenol derivatives and 2 equiv. of diazonium salt gave the monosubstituted product in the first case and a diadduct in the second case; X‐ray diffraction analysis revealed a highly symmetric structure for the latter. The different behaviors of hydroxy‐ and methoxy‐substituted compounds was particularly evident for phloroglucinol and 1,3,5‐trimethoxybenzene and may be rationalized on the basis of the different electronic effects of the substituents. The propensities of the aromatic rings to undergo H/D exchange reactions were investigated for a series of substrates, and a comparison of the results obtained provided new insights into this phenomenon and permitted a better explanation of the findings reported here; a new particular interaction competes with the formation of a proton–phloroglucinol σ complex.

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Hydroxy‐ and Methoxybenzene Derivatives with Benzenediazonium Salts ― Chemical Behavior and Tautomeric Problems

et al. 2017

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Explosion bei der Herstellung von Trinitrosophloroglucin

Cited by 1 publication

References 5 publications

Hydroxy‐ and Methoxybenzene Derivatives with Benzenediazonium Salts ― Chemical Behavior and Tautomeric Problems

Hydroxy‐ and Methoxybenzene Derivatives with Benzenediazonium Salts ― Chemical Behavior and Tautomeric Problems

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