1.3- Benzenediols hydrogenation

Very recently, MacGillivray et al. succeeded in the supramolecular construction of molecular ladders in the solid state using a linear template approach [48]. They designed the cocrystals 1,3-benzenediol (resorcinol) or a derivative with an all-trans-bis(4-pyridyl)butadiene or hexatriene, in which two resorcinol molecules preorganize two polyene molecules through two hydrogen bond interactions, for [2-1-2] photoaddition (Scheme 5). In this design, two polyenes would... 

An exception to the generalization that C—O bonds to aromatic systems are difficult both to make and to break is provided by reversible conversion of benzenediols and 1- or 2-naphthalenols to the corresponding amines, usually at elevated temperatures with sodium hydrogen sulfite or an acidic catalyst. The sodium hydrogen sulfite-induced reaction is called the Bucherer reaction ... 

Kawai H, Kaloono R, Nishimura K, Matsuda S, Fujiwara K, Tsuji T, Suzuki T. Positive homotropic allosteric binding of benzenediols in a hydrindacene-based exoditopic receptor co-operativity in amide hydrogen bonding. J. Am. Chem. Soc. 2004 126 5034-5035. 

The solid o-nitrophenol was neither stabilized nor destabilized relative to prediction neither is ca 9 kJ mol a very large stabilization for two possible pairs of hydrogen-bonding hydroxy/nitro substituents in 4,6-dinitro-l,3-benzenediol. Accordingly, the reaction depicted in eqnation 17 is only 3.6 kJ moH endothermic. 

Benzenediols—see also Acylbenzenediols, Alkylbenzenediols, Chlorobenzenediols, Dihydroxybenzenes, Nitrobenzenediols thermochemistry of 242-246 Benzimidazoles, hydrogen transfer in 1025 Benzoates—see Aryl benzoates, Heptabenzoates... 

Oxidation of hydroquinone (1,4-benzenediol) produces a compound known as /)-benzoquinone. The oxidation can be brought about by mild oxidizing agents, and, overall, the oxidation amounts to the removal of a pair of electrons (2 e") and two protons from hydroquinone. (Another way of visualizing the oxidation is as the loss of a hydrogen molecule, H H, making it a dehydrogenation.)... 

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