4- Nitrophenyl vinyl ether

The reaction of acyclic ADC compounds with monoenes has already been discussed in Sections III,B and IV,B. In certain cases the major reaction pathway involves addition of the ADC compound as a 47r component, to the monoene to give 1,3,4-oxadiazines (Scheme 1). 1,3,4-Oxadiazines are the major or sole products from the reactions of ADC compounds with indene,80 and 4-nitrophenyl vinyl ether,90 and from the reaction of azodibenzoyl with enamines and enol ethers.91 93 Norbornadiene also gives a 1,3,4-oxadiazine (42) with ADC compounds.82 However, benzonorbornadiene behaves differently, and the major product from the reaction with PTAD has the structure 119.205 Other bicyclic monoenes react similarly.206 1,3,4-... 

The relative stability of l, 2 -epoxyvinylbital, and the great instability of its diol, can be gainfully compared with the fate of the corresponding metabolites of phenyl vinyl ether (10.69, R = H) and 4-nitrophenyl vinyl ether (10.69, R = N02), two mutagenic and tumorigenic compounds [144] [145]. Their primary metabolic route is by vinyl epoxidation to the corresponding... 

M. Isobe, T. Sone, E. Takabatake, An Unstable Epoxy Intermediate Formed by the Microsomal Oxidation of 4-Nitrophenyl Vinyl Ether , Chem. Pharm. Bull. 1988, 36, 2267 -2269. 

Materials. CEVE and 4-nitrophenyl vinyl ether (VNP) were synthesized and purified as reported earlier (12,13), respectively. 2-(4-Nitrophenoxy)ethyl vinyl ether (NPVE) (m.p. 72-73°C) was prepared by reacting of potassium 4-nitrophenoxide (PNP) (142 g 0.8 mol) and CVE (842 g 7.9 mol) using tetra-n-butylammonium bromide (TBAB) (4.0 g 12 mmol) as a phase transfer catalyst at the boiling temperature of CVE for 12 h. The potassium chloride produced was filtered off, the filtrate washed with water, excess CVE evaporated, and then the crude product was recrystallized twice from n-hexane. (Yield 61.7%. IR (KBr) 1630 (C=C), 1520 (-N02), and 1340 cm-1 (-N02).) Elemental analysis on the product provided the following data Calculated for C10HnNO4 C, 57.40%, H, 5.30%, N, 6.69%. Found C, 57.49%, H, 5.3%, N, 6.72%. 

As model compounds, we used isopropyl p-nitrobenzoate for poly(vinyl p-nitrobenzoate), p-nitrophenyl iaobutyrate for poly(p-nitrophenyl acrylate), p-nitrocumene for poly(p-nitrostyrene), and p-nitrophenyl isopropyl ether for poly(p-nitrophenyl vinyl ether). The structure and Hammett s a constants of these model compounds and the chain transfer constants of polystyrene radicals to these compounds are given in Table 5 (3). 

Allyl 4-toluenesulfonate, 3315 f Allyl vinyl ether, 1904 f 3-Aminopropene, 1254 3-Azidopropene, 1188 f l-Bromo-2-butene, 1548 f 3-Bromo-l-propene, 1153 /V-Chloroallylaminc. 1202 l-Chloro-4-(2-nitrophenyl)-2-butene, 3270 f 3-Chloropropene, 1158 f 3-Cyanopropene, 1465 f Diallylamine, 2450 f Diallyl ether, 2431... 

Liq = liquid membrane with ion-exchange solution into the porous diaphgragm PVC = plasticized poly(vinyl chloride) Epoxy = conductive epoxy resin membrane. BA = benzyl alcohol BEHP = bis(2-Ethylhexyl)phthalate DA = 1-decanol DBP = dibutyl phthalate DBS = dibutyl sebacate DNP = dinonyl phthalate DOP = dioctyl phthalate NB = nitrobenzene NPOE = 2-nitrophenyl octyl ether NT = 2-nitrotoluene or 4-nitrotoluene OA = 1-octanol. 

Vinyl ethers react in the same manner, the reaction being somewhat slower. a-Methoxystyrene and -nitrophenyl azide yielded (93%) the triazoline 237 °°. 

Hydroxyl group Adamantane-l-carboxylic acid chloride. 0-Benzoylpropionic acid. Ethyl vinyl ether. 4-Methoxy-5,6-dihydro-2H-pyrane. p-Nitrophenyl chloroformate. 

In this work, an ionophore-based solvent polymeric membrane is cast on top of the PEDOT PSS channel in order to obtain an ion-selective organic electrochemical transistor (IS-OECT). The polymeric membrane is composed of 2-nitrophenyl octyl ether (o-NPOE, 57.2% ww), poly(vinyl chloride) (PVC, 27.9% ww), V.. V.. V. . V -i( I i i( ycloli( xyl-3-oxapentanedianii(le (ETH 129, 9.6% ww) and potassium tetrakis(4-chlorophenyl)borate (KTpCIPB, 5.4% ww), where ETH 129 is a Ca2+-selective ionophore. The channel region of the transistor that is coated by the Ca2+-selective membrane is immersed in an aqueous solution containing 0.1 M KC1 as a background electrolyte and... 

Representative procedure for the gold-catalyzed Gosteli-Claisen rearrangement/ cycloisomerization of alkoxycarbonyl-substituted propargyl vinyl ethers. Isopropyl 4,5-dimethyl-3-(4-nitrophenyl)juran-2-carboxylat ... 

Andersson, C.M. and Hallberg, A. (1988) Regioselective palladium-catalyzed arylation of vinyl ethers with 4-nitrophenyl triflate. Control by addition of halide ions. J. Org. Chem., S3, 2112-4. 

To enhance the permeation efficiency and selectivity of the polymeric membrane separation, a novel polymeric plasticizer membrane which is composed of cellulose triacetate (CTA) as a membrane support, o-nitrophenyl octyl ether (NPOE) as a membrane plasticizer, and trioctylmethylammonium chloride (TOMAC) as an anion-exchange carrier has been developed. Compared with the poly (vinyl chloride) plasticizer membrane which is widely used for ion-selective electrode, the CTA membrane can contain a larger amount of plasticizer due to a high affinity between CTA and NPOE (25). Thus the plasticizer (NPOE) solubilized in the membrane acts effectively as an organic medium for the carrier mediated membrane separation (25-29). 

Sales et al. (2001) developed a potentiometric sensor for the determination of tartaric acid. Tartrate-sensitive electrodes were constructed, comprising poly(vinyl chloride) membranes. Various membrane compositions were evaluated and the one combining an ionic sensor (bis(triphenylphosphoranylidene)ammonium chloride), 4-ferf-octylphenol, and o-nitrophenyl octyl ether was selected. The analytical characteristics of this electrode were evaluated using a single-line flow injection manifold. The accuracy of the developed method was demonstrated for the determination of tartaric acid in red and white wine samples. 

Poly(vinyl chloride) (PVC) with an average polymerization degree of 1100 was purified by reprecipitation from THF in methanol. The plasticizers or membrane solvents, di-n-octylphthalate (DOP), o-nitrophenyl octyl ether (NPOE), and 2-fluorophenyl-2-nitrophenyl ether (FPNPE) were obtained from Dojindo Laboratories. The lipophilic salt, sodium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate (NaTFPB), was obtained from Tokyo Chemical Industry Co., Ltd. and Dojindo Laboratories. 

Organic azides combine with open-chain and cyclic eno) ethers to give A -triazolines in high yield. The addition is stereospecific cis and the orientation process is determined by electronic effects.145-160 The triazolines are unstable above 100° and can decompose in mainly two ways. 44 Triazolines from the open-chain enol ethers, vinyl butyl ether, /S-ethoxypropene, and a- and /3-methoxystyrene, eliminate alcohol thermally and are converted into 1,2,3-triazoles. For example, the triazoline 67 from /J-ethoxypropene 66 and p-nitrophenyl azide decomposes quantitatively at 150° into l-(p-nitrophenyl)-5-methyl-1,2,3-triazole (68). 

AA AAm Con A DSS DSS-gel LCST MAPTAC MBA MP MP-gel NIPA ONPG PVMA SSPG Tc TMED acrylic acid acrylamide concanavalin A dextran sulfate sodium gel containing Con A/DSS complex lower critical solution temperature [(methacrylamide)propyl]trimethylammonium chloride /V,/V -methylenebis(acrylamide) a-methyl-D-mannopyranoside gel containing Con A/MP complex /V-isopropylacrylamide O-nitrophenyl-P-D-galactopyranoside poly(vinyl methyl ether) stimulus-sensitive polymer gel transition temperature /V,/V,/V, /V -tetramethylethylenediamine... 

The O-dealkylation of organophosphorus triesters differs from the above reactions in that it involves the dealkylation of an ester rather than an ether. The reaction was first described for the insecticide chlorfenvinphos (Figure 10.2B), but is now known to occur with a wide variety of vinyl, phenyl, phenylvinyl, and naphthyl phosphates and the thionophosphate triesters. At least one phosphonate, O-ethyl O-p-nitrophenyl phenylphosphonate (EPNO), is also metabolized by this mechanism. 

---