Chloroaniles

The Patterno-Buchi coupling of various stilbenes (S) with chloroanil (Q) to yield fran -oxetanes is achieved by the specific charge-transfer photo-activation of the electron donor-acceptor complexes (SQ). Time-resolved spectroscopy revealed the (singlet) ion-radical pair[S+% Q" ] to be the primary reaction intermediate and established the electron-transfer pathway for this Patterno-Buchi transformation. Carbonyl quinone activation leads to the same oxetane products with identical isomer ratios. Thus, an analogous mechanism is applied which includes an initial transfer quenching of the photo-activated (triplet) quinone acceptor by the stilbene donors resulting in triplet ion-radical pairs. ... 

An Ion Chromatograph has been successfully automated by interfacing it to an automatic sampler (7). Continuous unattended analysis was possible, the actual number of samples analyzed being limited by the ionic capacity of the suppressor column. The automated Ion Chromatograph was used to analyze soluble sulfates, ammonia and alkyl amines in stack and automobile exhqust samples. Excellent agreement between IC and automated barium chloroanilate titration for sulfate was obtained with a relative standard deviation less than 5%. 

In contrast to the reactions of pyrans with electrophiles and nucleophiles, oxidations of 2-amino-4H-pyrans are represented by very few examples. Oxidizing of 281 into 2-iminopyrans 296 with chloroanil or dichlor-odicyanoquinone (DDQ) (04JME6299) can be used to protect the amino group in Sandmeyer reaction (297), or to introduce a methyl group into position 4 of pyran 298. The latter is essential because the corresponding acetophenones do not give 298 with MN and aminophenols (Scheme 125). 

The last reagent is added as a moderator to prevent a runaway reaction nitrobenzene, or an alternative oxidant (iodine or chloroanil are often recommended), is required to convert the product, 1,2-dihydroquinoline, into quinoline. 

A homologous series of nickel(II) complexes with the general formula Ni2L(tren)2(BPh4)2 has been prepared with the dianionic ligands L which arise from the deprotonation of the neutral molecules (202)-(207).1604-1606 All of these complexes are assumed to exhibit the same dinuclear structure (208) as found in the complex with L = chloroanilate (202).1604... 

The reduction of azepinone 484 leads to 1,2,3,4-tetrahydroderivative 485, whereas dehydrogenation of 484 by chloroanil results in 1H-naphtho[Mazepine-2-one 486 (76JHC371). The interesting conversion resulting in l//-l-methyl-3-formyl-7-methoxynaphtho[bc]azepine-2-one 490 occurs on interaction of 4-methoxy-8-(N-methyl-N-acetyl)aminonaphthal-dehyde 487 with the Vilsmeier reagent (86ZOR2394). It was assumed that compounds 488 and 489 are intermediates in this reaction. 

Me PhCO 2-ClC6H4CO 4-ClC6H4CO Chloroanil, xylene, reflux, 12 h 35-48 01JHC829... 

Scheme 2.32 Formation of optically active a-hydroxyesters by reaction of acid chlorides with benzoylquinidine acting a catalytic chiral nucleophile, followed by [4+2]-cycloaddition with o-chloroanil.

Kochi and coworkers reported the photochemical addition of various stilbenes and chloroanil (53) which is controlled by the charge-transfer (CT)... 

Br2 = bromine, TCNE = tetracyanoethylene, CA = chloroanil). Data from refs. [23a, 23g]. 

Dioxin and furan contamination in chloroanil and carbazole violet"... 

SYNS l-AMINO-2-CHLOROBENZENE o-CHLO-RAMLINE o-CHLORO. NILINE o-CHLOROANIL-INE, Uquid o-CHLOROANILINE, soUd 2-CHLORO-BENZENAMINE (9CI) FAST T ELLOW GC BASE... 

Koizumi, S. and Matsunaga, Y. (1972). Polymorphism and physical properties of the l,6-diaminopyrene-/ -chloroanil and related molecular complexes. Bull. Chem. Soc. Jpn., 45,423-8. [82]... 

In the case of the previously discussed [2]catenane 18 + shown in Figure 30, switching from the more stable translational isomer (which contains a TTF unit inside the tetracationic cyclophane) to a less stable one can be obtained not only by oxidation of the TTF unit, but also by addition of o-chloroanil. H NMR spectroscopy shows that o-chloroanil gives an adduct, presumably CT in nature, with the TTF unit which locks this unit alongside the cavity of the cyclophane. On addition of Na2S205 the adduct is destroyed and the original isomer with the TTF unit inside the cavity of the cyclophane is restored [59, 66[. 

Irradiation of a donor monomer-electron acceptor charge transfer complex, e.g. N-vinylcarbazole-sodium chloroaurate (2), -nitrobenzene (2) or -p-chloroanil (3) and -p opiolactone-uranyl nitrate (h), results in the initiation of cationic polymerization. 

Reaction of ketenylidene- or thioketenylidenetriphenylphosphoranes with a,P-unsaturated carbonyls, e.g. 2-benzylidene-l,3-indandione yields pyranones and thioxopyranones IQP Treatment of the same phosphoranes with o-chloroanil (tetrachloro-l,2-benzoquinone) yields 71Ketenylidenetriphenylphosphorane... 

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