Naphthalene, iodo

Benzene- 1,2-diacetonitriles e.g. 19, in the presence of hydrogen bromide in acetic acid, or in diethyl ether, cyclize to 4-bromo-l //-3-benzazepin-2-amines, e.g. 20a.41,42 l//-Naphtho[2,3-t/]azepines, e.g. 22a, are prepared in a similar manner from naphthalene-2,3-diacetonitriles, e.g. 21.41 Replacement of hydrogen bromide by hydrogen iodide yields the corresponding 4-iodo derivatives, e.g. 20b and 22b. 

The vapour-pressure equation (22) has been verified for brom-and iodo-naphthalene by L. Rollo(7) (1909), and for toluene, naphthalene, and benzene by J. T. Barker (1910). The latter finds that the solid and liquid states give the same chemical constant, which is in agreement with Nemst s theory. 

Nitro-4-lodo-1-Oxy-Naphthalene (2-Nitro-4-iodo-l-naphthol). (02N)C1oHs(I).OH, mw 315.09, N 4.45%, OB to C02 -101.56%, clear golden needles, mp 115° (decompn). Prepn from 4-nitro-2-acetoxymercuric-naphthol-(l) by reacting with iodine... 

TETRAHYDRO-2-IODO-, METHYL ESTER, 51,112 Naphthalene-l-carbonitrile, 50,20... 

The difference in the reactivity of benzylic versus aromatic halogens makes it possible to reduce the former ones preferentially. Lithium aluminum hydride replaced only the benzylic bromine by hydrogen in 2-bromomethyl-3-chloro-naphthalene (yield 75%) [540]. Sodium borohydride in diglyme reduces, as a rule, benzylic halides but not aromatic halides (except for some iodo derivatives) [505, 541]. Lithium aluminum hydride hydrogenolyzes benzyl halides and aryl bromides and iodides. Aryl chlorides and especially fluorides are quite resistant [540,542], However, in polyfluorinated aromatics, because of the very low electron density of the ring, even fluorine was replaced by hydrogen using lithium aluminum hydride [543]. 

Naphthalene carbamic acid, l,2,3,4-tetrahydro-2-iodo-, methyl... 

Halogen shifts have been found for tungsten, with assumed formation of iodovinylidenes in reactions of 1-iodo-l-alkynes with W(CO)5(thf) en route to cyclization of 2-(iodoethynyl)styrenes to naphthalenes and of iodo-alkynyl silyl enol ethers [147], while more substantial confirmation is found in Mn =C=C(I)CH (OR)2 (CO)2Cp [R = Me, Et (OR)2 = 0(CH2)30], of which the XRD structure of Mn =C=C(I)CH(OMe)2 (CO)2Cp was determined [148]. 

Vapor phase pyrolysis of 2-aminobiphenyl in chloroform at 350°C produces carbazole,as does heating at 500-800°C in a high-frequency glow discharge at 25-34 A small amount (11%) of carbazole 280 was formed during the reaction of 281 with copper-potassium carbonate and 1-iodo-naphthalene in nitrobenzene. ... 

This latter equation correctly predicts the rates at which 1-iodo-naphthalene quenches triplet naphthalene in several fairly viscous solvents.165 It also correctly predicts the rate at which 2,5-dimethyl-2,4-hexadiene quenches triplet valerophenone in cyclooctane if the ketone s triplet lifetime is the same as that estimated from quenching experiments and from the flash spectroscopically measured rate constant for diffusion-controlled quenching in benzene.183... 

Pyrrolidines piperidines.D Suitably unsaturated a-iodo (or a-bromo) esters cyclize to pyrrolidines or piperidines in the presence of this Pd(0) catalyst and 1,8-bis(dimethylamino)naphthalene (proton sponge). 

In the reaction of 1-naphthoxide ions, a mixture of 2- and 4-aryl-, along with 2,4-diaryl-l-naphthol, is formed. However, substitution occurs only at C4 with the 2-Me-substituted anion (50-70% yields) [1[. On the other hand, 2-naphthoxide ions react with ArX to give substitution only at Cj of the naphthalene ring [32, 33]. The reactivity of the 2-naphthoxide ions allows the synthesis of naphthylpyridines, naphthylquinolines, and naphthylisoquinolines via their coupling reactions with the corresponding halo arenes, in good to excellent yields (50-95%) [33], The photostimulated reaction between 2-naphthoxide ions and l-iodo-2-methoxy-naphthalene was explored in liquid ammonia, as a novel approach to the synthesis of [1,1 ] binaphthalenyl-2,2 -diol (BINOL) derivatives (Scheme 10.23). This procedure has also been applied to the synthesis of BINOL in moderate yield (40%), which represents the first report of an SRN1 reaction in water [34]. 

When [bis(acyloxy)iodo]arenes have electron-withdrawing groups either in the phenyl ring or in the acyloxy moiety, their oxidizing power increases generally. In a comparative study of the conversion of 1,5-dihydroxy-naphthalene to juglone, the following yields were obtained, under similar conditions [62] ... 

The thermolysis of iodonium salts in which their counteranion is a halide may be performed in the molten state or in solution the products are an iodoarene and a haloarene. The reaction which is a nucleophilic aromatic substitution is, however, not preparatively useful an exception was 3-indolyl phenyliodonium trifluoroace-tate which on heating with various chlorides and bromides in DMSO afforded variable mixtures of 2- and 3-haloindoles. By contrast, the jV-methyl and N-benzyl analogues gave only 2-chloro derivatives [58], Sometimes useful products may be obtained from the thermolysis of dibenziodolium or other heterocyclic salts, as exemplified in the preparation of l-iodo-2-(2-iodophenyl)naphthalene [59] ... 

When the reaction of the 2-methyl-1-naphthoxide ions was performed with 1-iodo-, 2-iodo-, 6-(/-Pr)-2-iodo-, or 3,5-di-(OMe)-2-iodo naphthalenes only the 4-substitution product was formed in 50-70% yield. In the photostimulated reaction of 4-substituted... 

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