Cyanophenols

Reactions with Amines and Amides. Hydroxybenzaldehydes undergo the normal reactions with aUphatic and aromatic primary amines to form imines and Schiff bases reaction with hydroxylamine gives an oxime, reaction with hydrazines gives hydrazones, and reactions with semicarbazide give semicarbazones. The reaction of 4-hydroxybenzaldehyde with hydroxylamine hydrochloride is a convenient method for the preparation of 4-cyanophenol (52,53). 

Electron impact fragmentation studies on 1,2-benzisoxazoles and benzoxazole indicate that isomerization takes place before degradation. Shape analysis and metastable ion abundances in the mass spectra indicate that isomerization to o-cyanophenols occurred prior to degradation by loss of CO or NCH (75BSB207). 

MILLER - SNYDER Aiyl Cyanide Synthesis Synthesis of benzonitnies from aldehydes via oxime ethers Formation of p-cyanophenol from p nrtrobenzaldoxime and p-nitiobenzonitnle (used as a sometimes recyclable chain carrier)... 

Thereacdon of -cyanophenol v/itho-dinitrobenzenein the presence of KFin DMSO gives the corresponding diaryl ether in 95% yield fEq 9 4 ... 

Desulfitobacterium chlororespirans can use ortho-substituted phenols as electron acceptors for anaerobic growth, and is able to debrominate 2,6-dibromo-4-cyanophenol (Bromoxynil) and 2,6-dibromo-4-carboxyphenol. In contrast, 2,6-diiodo-4-cyanophenol (loxynil) was deiodinated only in the presence of 3-chloro-4-hydroxybenzoate (Cupples et al. 2005). 

Two different approaches have been used to determine phenols without derivatization. In the first, the corresponding oxalate esters were synthesized in the traditional way (i.e., using oxalyl chloride and triethylamine) [111, 112]. Pen-tachlorophenol, 1-naphthol, bromofenoxim, bromoxynil, and /t-cyanophenol were treated this way, after which the POCL resulting from their reaction was measured in a static system. The second approach exploits the oxidation reaction between imidazole and hydroxyl compounds at an alkaline pH, where hydrogen peroxide is formed [113]. Polyphenols, e.g., pyrogallol, pyrocatechol, and dopa-... 

Fig. 10 The use of a cationic hapten [22] mimics the transition state of the base-promoted decomposition of substituted benzisoxazole [20] to cyanophenol [21] and also acts as a bait to induce the presence of an anion in the combining site that...

FIGURE 6 Effect of p-cyanophenol on the separation of perchlorate. Column 4x250mm lonPac ASII. Flow rate I.OmLmin. Injection volume 25pL. Detection suppressed conductivity utilizing the Anion Self Regenerating Suppressor (4mm), recycle mode. Ion I—perchlorate (20mgL" ). (a) Eluent lOOmM NaOH. (b) Eluent 50 mM NaOH and 5mM p-cyanophenol. 

---