Indene 1-carboxylic acid

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. 

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. 

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)... 

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. 

Positive photoresists, by contrast, are based on water-soluble novolak resins with naphthalene diazoquinone sulfonate (NDS) as the photosensi-tiser. On photolysis the NDS causes a rearrangement in the polymer to yield nitrogen gas plus an indene carboxylic acid. This latter functional group considerably increases the solubility of the polymer, hence solubilising those areas of the polymer that had been exposed to light. 

CN [2S-(2a,5a,6P)]-6-[[3-[(2,3-dihydro-l/7-inden-5-yl)oxy]-l,3-dioxo-2-phenylpropyl]amino]-3,3-dimethyl-7-oxo-4-thia-l-azabicyclo[3.2.0]heptane-2-carboxylic acid... 

CN 6-chloro-5 -cyclohexyl-2,3-dihydro-1 /7-indene-1 -carboxylic acid... 

C jH2,NOSi) see Indanorex (lS-cii)-2,3-dihydro-l//-indene-l,2-diol (G7H10O2 6752S-22-7) see Indinavir sulfate (laS)-la,6a-dihydro-6//-indenori,2-6]oxirene (CgHjO 67528-26-1) see Indinavir sulfate (2,3-dihydro-l//-inden-4-yl)carbamimidothioic acid methyl ester monohydriodide (C, H 1N2S 40507-77-5) see Indanazoline 23-dibydro-l//-indole-2-carboxylic acid ethyl ester (C iH, N02 50501-07-0) see Perindopril... 

The use of phenolic polymers in photocrosslinkable systems usually involves multicomponent systems which incorporate polyfunctional low molecular weight crosslinkers. For example, Feely et al. [9] have used hydroxymethyl melamine in combination with a photoactive diazonaphthoquinone which produces an indene carboxylic acid upon irradiation to crosslink a novolac resin. Similarly, Iwayanagi et al. [10] have used photoactive bisazides in combination with poly(p-hydroxy-sty-rene) to afford a negative-tone resist material which does not swell upon development in aqueous base. 

The workhorse of the VLSI industry today is a composite novolac-diazonaphthoquinone photoresist that evolved from similar materials developed for the manufacture of photoplates used in the printing industry in the early 1900 s (23). The novolac matrix resin is a condensation polymer of a substituted phenol and formaldehyde that is rendered insoluble in aqueous base through addition of 10-20 wt% of a diazonaphthoquinone photoactive dissolution inhibitor (PAC). Upon irradiation, the PAC undergoes a Wolff rearrangement followed by hydrolysis to afford a base-soluble indene carboxylic acid. This reaction renders the exposed regions of the composite films soluble in aqueous base, and allows image formation. A schematic representation of the chemistry of this solution inhibition resist is shown in Figure 6. 

Bromine-atom atomic resonance absorption spectrometry (ARAS) has been applied to measure the thermal decomposition rate constants of CF3Br in Kr over the temperature range 1222-1624 K. The results were found to be consistent with recently published theory. The formation of cyclopent[a]indene and acenaphthylene from alkyl esters of biphenyl-mono- and -di-carboxylic acids has been observed in flash vacuum pyrolyses at 1000-1100 °C. The kinetics and mechanisms of free-radical generation in the ternary system containing styrene epoxide, / -TsOH, and i-PrOH have been examined in both the presence and absence of O2. ... 

Indanone, see Fluorene l-Indanone-7-carboxylic acid, see Acenaphthene Indene, see Di-n-butyl phthalate lodoformaldehyde, see Methyl iodide... 

The photoactive compounds, or sensitizers, that are used in the formulation of positive photoresists, are substituted diazonaphthoquinones shown in Figure 17. The substituent, shown as R in Figure 17, is generally an aryl sulfonate. The nature of the substituent influences the solubility characteristics of the sensitizer molecule and also influences the absorption characteristics of the chromophor (79). The diazonaphthoquinone sulfonates are soluble in common organic solvents but are insoluble in aqueous base. Upon exposure to light, these substances undergo a series of reactions that culminate in the formation of an indene carboxylic acid as depicted in Figure 17. The photoproduct, unlike its precursor, is extremely soluble in aqueous base by virtue of the carboxylic acid functionality. 

At the present time, most of the positive photoresists used in the manufacture of microcircuits consist of a low molecular weight phenolic resin and a photoactive dissolution inhibitor. This composite system is not readily soluble in aqueous base but becomes so upon irradiation with ultraviolet light. When this resist is exposed, the dissolution inhibitor, a diazoketone, undergoes a Wolff rearrangement followed by reaction with ambient water to produce a substituted indene carboxylic acid. This photoinduced transformation of the photoactive compound from a hydrophobic molecule to a hydrophillic carboxylic acid allows the resin to be rapidly dissolved by the developer. (L2,3)... 

The pH-rate profiles of the enol of l-indene-3-carboxylic acid and of its ketene precursor, formed from either l-diazo-2( 1 //jnaphthalenone or 2-diazo-l(2//)naphthalenone by photochemical deazotization and Wolff rearrangement, are shown in Fig. 5.36 The first and second acidity constants of the diol, p = 1.9 and p aE = 8.3, are evident from the downward curvature of log (k /s-1) at these pH values. The photo-Wolff rearrangement of diazonaphthoquinones is the active principle of Novolak photoresists. 

Fig. 5 pH rate profile of benzofulvene-l,l-diol, the enol of l-indene-3-carboxylic acid, and its ketene precursor.36... 

Nuclear tunnelling in the aqueous iron (2+)-iron (3+) electron transfer has been investigated467 and the rate enhancement for H2O has been assessed to be 65 times the classical rate, and that for D2O 25 times the classical rate, yielding a H/D isotope effect of 2.6. The occurrence of the general base catalysis and sizable primary D KIEs indicated that the isomerization of l//-indene-l-carboxylic acid to l//-indene-3-carboxylic acid in aqueous solution takes place through an enolization-reketonization sequence468. Kinetic HH/HD/DD isotope and solvent effects have been used in a dynamic NMR study469 of the tautomerization of 15N-and 2H -labelled bicyclic oxalamidines. 

Octahydro-7-methoxy-l-oxo-lf/-indene-4-carboxylic acids and -4-carboxylates Photochemical Addition of Methanol to Racemic Enones General Procedure24 ... 

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