Indene, acidity

It is known that the diazo sensitizer is temperature sensitive and decomposes almost completely on heating above 110°c. for 30 min. The decomposition products in the presence of moisture (in the atmosphere) are nitrogen (N ) and indene acid, a base developer soluble material. On extended heating at higher temperature there is a marked decrease in the dissolution rate of both P(MMA)(see figure 1) and the photo resist (figure 2). 

When side chains of two or more different kinds are attached to a cyclic component, only the senior side chain is named by the conjunctive method. The remaining side chains are named as prefixes. Likewise, when there is a choice of cyclic component, the senior is chosen. Benzene derivatives may be named by the conjunctive method only when two or more identical side chains are present. Trivial names for oxo carboxylic acids may be used for the acyclic component. If the cyclic and acyclic components are joined by a double bond, the locants of this bond are placed as superscripts to a Greek capital delta that is inserted between the two names. The locant for the cyclic component precedes that for the acyclic component, e.g., indene-A - -acetic acid. 

Few appHcations for fluoronaphthalenes and related polycycHc stmctures have materialized. The fused-ring bicycHc, suHndac [38194-50-2] a monofluorinated indene-3-acetic acid, is used as an antiinflammatory agent. 

The main impurity in cmde 78°C coal-tar naphthalene is sulfur which is present in the form of thionaphthene (1—3%). Methyl- and dimethylnaphthalenes also are present (1—2%) with lesser amounts of indene, methylindenes, tar acids, and tar bases. 

Such copolymers of oxygen have been prepared from styrene, a-methylstyrene, indene, ketenes, butadiene, isoprene, l,l-diphen5iethylene, methyl methacrjiate, methyl acrylate, acrylonitrile, and vinyl chloride (44,66,109). 1,3-Dienes, such as butadiene, yield randomly distributed 1,2- and 1,4-copolymers. Oxygen pressure and olefin stmcture are important factors in these reactions for example, other products, eg, carbonyl compounds, epoxides, etc, can form at low oxygen pressures. Polymers possessing dialkyl peroxide moieties in the polymer backbone have also been prepared by base-catalyzed condensations of di(hydroxy-/ f2 -alkyl) peroxides with dibasic acid chlorides or bis(chloroformates) (110). 

The process by which a solubility differential between exposed and unexposed areas occurs is well known (74). Photodegradation products of the naphthoquinone diazide sensitizer, eg, a l,2-naphthoquinonediazide-5-sulfonic acid ester (11), where Ar is an aryl group, to an indene carboxylic acid confers much increased solubility in aqueous alkaline developer solutions. 

Coumarone—Indene Kesins. These should be called polyindene resins (17) (see Hydrocarbon resins). They are derived from a close-cut fraction of a coke-oven naphtha free of tar acids and bases. This feedstock, distilling between 178 and 190°C and containing a minimum of 30% indene, is warmed to 35°C and polymeri2ed by a dding 0.7—0.8% of the phenol or acetic acid complex of boron trifluoride as catalyst. With the phenol complex, tar acids need not be completely removed and the yield is better. The reaction is exothermic and the temperature is kept below 120°C. When the reaction is complete, the catalyst is decomposed by using a hot concentrated solution of sodium carbonate. Unreacted naphtha is removed, first with Hve steam and then by vacuum distillation to leave an amber-colored resin. It is poured into trays, allowed to cool, and broken up for sale. 

Thiacyclotrideca-2,4,10,12-tetraene-6,8-diyne 1 -oxide, 5,10-dimethyl- HNMR, 7, 717 (75JA640) 4-Thia-2,6-diazabicyclo[3.2.0]heptane-2-carboxylic acid, 7-OXO-, t-butyl ester X-ray, 7, 349 (B-72M151201) 5H-2aA -Thia-2,3-diazacyclopent[cd]indene, 2,3-dimethyl-6,7-dihydro-X-ray, 6, 1054 (72ACS343)... 

The raw material has to be washed to remove impurities. Diluted sodium hydroxide allows the removal of phenols and benzonitrile, and diluted sulphuric acid reacts with pyridine bases. The resulting material is distilled to concentrate the unsaturated compounds (raw feedstock for coumarone-indene resin production), and separate and recover interesting non-polymerizable compounds (naphthalene, benzene, toluene, xylenes). Once the unsaturated compounds are distilled, they are treated with small amounts of sulphuric acid to improve their colour activated carbons or clays can be also used. The resulting material is subjected to polymerization. It is important to avoid long storage time of the feedstock because oxidation processes can easily occur, affecting the polymerization reaction and the colour of the coumarone-indene resins. 

Coumarone-indene resins were produced by adding sulphuric acid to the stirred feedstock at 20-35°C, taking care to produce a good dispersion of the sulphuric acid to avoid scorching (dark-coloured resins are obtained), and to con-... 

As enolate precursors can be used CH-acidic carbonyl compounds such as malonic esters, cyanoacetic esters, acetoacetic esters and other /3-ketoesters, as well as aldehydes and ketones. Even CH-acidic hydrocarbons such as indene and fluorene can be converted into suitable carbon nucleophiles. 

Chemical Name 6-Chloro-5arboxylic acid Common Name —... 

The acidic solution, containing the 2-(2-dimethylaminoethyl)-1- [l-(2-pyridyl)-ethyl] -indan-Tol is heated on the steam bath for thirty minutes to effect dehydration to the desired indene derivative. The solution is cooled, made strongly basic with an aqueous solution... 

At 15 mm pressure the excess of 2-ethylpyridine is removed, at 120°C/0.5 mm some unreacted 2-(2-dimethylaminoethyl)-indene distills and at 165°-175°C/0.5 mm the 2-(2-dimethyl-aminoethyl)-3-[1-(2-pyridyl)-ethyl]-indene is collected. It may be converted to an aqueous solution of the dihydrochloride by dissolving it in the appropriate amount of dilute hydrochloric acid. 

To a solution of 1.0 gram of 2-(2-dimethylaminoethyl)-3-[ 1-(2-pyridyl)-ethyl]-indene in 10 ml of ethanol is added while stirring and heating 0.4 gram of maleic acid. On cooling the 2-(2-dimethylaminoethyl)-3-[ 1-(2-pyridyl)-ethyl]-indene maleate crystallizes, is filtered off, washed with a small amount of ethanol and recrystallized from ethanol, MP 158°C. 

Chemical Name (Z)-5-fluoro-2-methyl-1 [ [4-(methylsulfinyl)phenyl] methylene] -IH-indene-3-acetic acid... 

Highly substituted dimethyl 2,4-diphenyl-3-benzoxepin-l,5-dicarboxylate was converted by irradiation to an indene derivative 4 which had lost one benzoyl group by acidic hydrolysis.146... 

The epoxidation method developed by Noyori was subsequently applied to the direct formation of dicarboxylic acids from olefins [55], Cyclohexene was oxidized to adipic acid in 93% yield with the tungstate/ammonium bisulfate system and 4 equivalents of hydrogen peroxide. The selectivity problem associated with the Noyori method was circumvented to a certain degree by the improvements introduced by Jacobs and coworkers [56]. Additional amounts of (aminomethyl)phos-phonic acid and Na2W04 were introduced into the standard catalytic mixture, and the pH of the reaction media was adjusted to 4.2-5 with aqueous NaOH. These changes allowed for the formation of epoxides from ot-pinene, 1 -phenyl- 1-cyclohex-ene, and indene, with high levels of conversion and good selectivity (Scheme 6.3). 

A mixture of 2.0 mmol of a 1.6 N solution of butyllithium in hexane and 0.47 g (2.0 mmol) of(-)-spartcinc in 10 mL of diethyl ether is stirred for 15 min at — 78 rC then 0.26 g (2.0 mmol) of 1-methyl-l//-indene in 2 mL of diethyl ether are added. Stirring is continued for 30 inin at 20 °C, the mixture is cooled to — 70 CC and 2.5 mmol of the acid chloride in 2 mL of diethyl ether are added. After stirring for 4h the usual aqueous workup was accomplished by addition of 10 mL of diethyl ether and successive washing with 10 mL of 2 N aq HC1. water and sat. aq NtiCl, respectively, followed by chromatographic purification on silica gel with diethyl cthcr/pentane. 

Analogous to the allylsilane cyclizations, alkynylsilanes can also be used to synthesize 1,2-fused bicyclic compounds. The intramolecular addition of 4-[5-(trimethylsilyl)-3-pentynyl]-2-cyclo-hexenone proceeded smoothly in the presence of various Lewis acids, yielding functionalized cw-fused octahydro-5/f-inden-5-ones containing the synthetically useful terminal allene unit45. 

Indenes, 34 Indole [ 1H Indole], 10 INDOLE, 3-BENZOYL- [METI1ANONE, 1//-INDOL-3-YLPHENYL-], 8 INDOLE, 3-BENZYL- [lff-INDOLE, 3-(PHENYLMETHYL)-], 8 INDOLE, 5-CARBOETHOXY-2-METHYL-] 17/-1NDOLE-5-C ARBOXYLIC ACID, 2-METHYL, ETHYL ESTER], 72 Indole, S-carlioethoxy-2-methyI-3-niethyl-thio-11H Indole-5-carboxyhc acid, 2-methyl-3-(methylthio)-, ethyl ester, 73... 

In his pioneering work, Sus (1944) assumed that the final product of photodediazoniation of 2,1-diazonaphthoquinone (10.75) is indene-l-carboxylic acid (10.79, not the 3-isomer 10.78). He came to this conclusion on the basis of some analogies (in addition to an elemental analysis). Cope et al. (1956) as well as Yates and Robb (1957) found that the infrared spectrum of the product was consistent with an a,P-unsaturated acid. Later, Melera et al. (1974) verified the structure 10.78 by H NMR spectroscopy. Friedrich and Taggart (1975) showed that the equilibrium between 10.78 and 10.79 at 233 K lies on the side of the latter, but 10.78 clearly predominates at or above 0°C. Ponomareva et al. (1980) showed that not only 2,1-, but also 1,2-diazo-naphthoquinone yields indene-3- and not -1-carboxylic acid. 

Hydrogenation, of gallic add with rhodium-alumina catalyst, 43, 62 of resorcinol to dihydroresorcinol, 41,56 Hydrogen peroxide, and formic acid, with indene, 41, 53 in oxidation of benzoic add to peroxy-benzoic add, 43, 93 in oxidation of ieri-butyl alcohol to a,a/r, a -tetramcthyltetra-methylene glycol, 40, 90 in oxidation of teri-butylamine to a,<, a, a -tetramethyltetra-methylenediamine, 40, 92 in oxidation of Crystal Violet, 41, 2, 3—4... 

Hydroxylamine-O-sulfonic acid for N-amination of pyridine, 43, 1 Hydroxylation of indene, 41, 53 2-Hydroxy-3-methylbenzoic add, oxidation to 2-hydroxyisophthalic acid by lead dioxide, 40, 48 Rydroxymethyleerrocene. 40, 52... 

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