Indene hydroxylation

Indene, 6, 7-dimethox y-3-meti iy l-2 -CARBETHOXY-, 40, 43 Indene, hydroxylation of, 41, 53 Indole, methylation to 1-methylindole, 40,68... 

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... 

Tetrahydroprotoberberines (59) having a phenolic hydroxyl group were heated in trifluoroacetic anhydride in a sealed tube to afford the indene derivatives (60) after treatment with methanol (Scheme 14) (57). The products formed through both C-14—N and C-8—N bond cleavage followed by ring closure. 

Chlordane is subject to hydrolysis via the nucleophilic substitution of chlorine by hydroxyl ions to yield 2,4,5,6,7,8,8-heptachloro-3a,4,7,7a-tetrahydro-4,7-methano-l//-indene which is resistant to hydrolysis (Kollig, 1993). The hydrolysis half-life at pH 7 and 25 °C was estimated to be >197,000 yr (Ellington et ah, 1988). 

Only polyarylallenes can be made in fair yield by heating the corresponding alcohols with either acetic anhydride or potassium bisulfate since the hydroxyl group is relatively labile [32]. The competing side reaction is the formation of indenes and dimers [33-36] (Eq. 29). 

Enantiomeric cyclic amides and imides, esters, ketones, 8- and 7-lactones, and alkyl-substituted indenes can be resolved on CTA-I without derivatization. Chiral alcohols can also be resolved without deiivatiza-tion, but the best results are obtained when they are converted to esters. In general, para-nitrobenzoic esters are recommended if the hydroxyl group is directly attached to the stereogenic center benzoate or para-biomobenzoate... 

Generally, arene(alkoxy)carbene chromium complexes react with aryl-, alkyl-, terminal or internal alkynes in ethers or acetonitrile to yield 4-alkoxy-l-naphthols, with the more hindered substituent ortho to the hydroxyl group . Upon treatment with alkynes, aryl(dialkylamino)carbene chromium complexes do not yield aminonaphthols, but they form indene derivatives . Vinyl(dialkylamino)carbene complexes, however, react with alkynes to yield aminophenols as the main products The solvent is one of the many factors that affects this type of reaction, for which the most important is the polarity and/or coordinating ability of the solvent. The Dotz benzannulation reaction yields either arene chromium tricarbonyl complexes or the decomplexed phenols, depending on the work-up conditions. Oxidative work-up yields either decomplexed phenols or the corresponding quinones. 

It has been noted in Section 4.4.1.1 that naphthalene dioxygenase from a strain of Pseudomonas sp. also carries out enantiomeric monooxygenation of indan and dehydrogenation of indene (Gibson et al. 1995), and the stereospecific hydroxylation of (R)-l-indanol and (S)-l-indanol to rfs-indan-l,3-diol and trans (lS,3S)-indan-l,3-diol (Lee et al. 1997) the indantriols are also formed by further reactions. Essentially comparable reactions have been observed with Rhodococcus sp. strain NCIMB 12038 (Allen et al. 1997). 

Hydroxyisophthalic acid, 40, 48 Hydroxylamine hydrochloride, reaction with ethyl carbamate to form hydroxyurea, 40, 60 Hydroxylation of indene, 41, 53... 

FIGURE 5.43 Photolysis of diazonaphthoquinone sulfonate esters (DNS) followed by (a) Wolff rearrangement to a ketene intermediate, which (b) reacts with water to form an indene carboxylic acid or (c) reacts with phenolic hydroxyl groups (in absence of water) to form ester linkages. 

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