Indanone, from indane

This reaction (13) is exothermic by 14 kJ mol-1 and so 2-benzoxazolinone seems to be nonaromatic. The same reaction enthalpy value as for 2-indanone (six n electrons), not far from indane (21 kJ mol-1), suggests that it lacks aromaticity other than found in its benzene ring, much as found for indane and the indanones. Admittedly, the enthalpy of formation of CH3NHCOOCH3(A,0-dimethylcar-bamate) is unknown however, we may estimate the value to be -420 kJ mol1 by assuming thermoneutrality for reaction 14 ... 

For qualitative analyses, the GC system was equipped with a J W Scientific HP-5 or a Supelco Simplicity 1 fiised-sUica capillary column. Injector and detector temperatures were set at 220 °C and 240 °C respectively the oven temperature was programmed from 60 to 230 °C at 40 °C min. Helium was employed as carrier gas (1 mL min ). Compound identification was based on a comparison of mass spectra with those of synthetic racemic and enantiomeric-enriched samples. The retention times for indan, 1-indanol and 1-indanone were 4.7 min, 5.9 min and 6.2 min respectively. 

Oxidation at the benzylic position of indane -with potassium permanganate (Eq. 3.30) gives indanone in good yields and no PTC is necessary [133]. In a two-phase system consisting of an aqueous solution of KMn04 and indane in benzene an 80 % yield can be obtained under a reduced pressure of ca. 450 Torr. The authors explain this effect by the size of the cavitation bubbles, which is dictated to some extent by the over pressure. An optimal energy transformation, from acoustic to chemical, can thus take place. 

Later it was described the synthesis of the donepezil HCI from 5,6-dimethoxy-2-(pyridin-4-yl)methylene-indan-l-one by the reaction with H2 over platinum dioxide at room temperature in acetic acid-methanol mixture to give 4-[(5,6-dimethoxy-l-indanon)-2-yl]methylpiperidine. The last one yielded donepesyl HCI by refluxing with benzyl bromide and triethylamine for 4 hours with the following addition of methanolic HCI (10%). 

The first of these alternative approaches started with commercially available indanone-3-carboxylic acid 23 (derived from phenylsuccinic anhydride via Friedel-Crafts chemistry). This indanone was a viable precursor to 6 through an aminomethyl homologation with cyanide or nitromethane (Scheme 3.10). Our intent was to obtain ester 25, which after reduction would afford methylamine 28, which in turn would cyclize to generate lactam 29, giving benzazepine 6 upon reduction. Stereocontrol in the homologation was unnecessary, as lactam 29 would theoretically provide a thermodynamic sink under epimerizing reaction conditions, capturing the desired di-indane isomer. 

Rhodococcus sp. 124 was isolated fi-om a toluene-contaminated aquifer and was found to oxidize indene to 1,2-indandiol and several other products. The undesired products 1-indenol and 1-indanone were formed directly from indene while racemic l-keto-2-hydroxy-indan was formed from the indandiols. Based on product formation profiles and induction experiments, 124 was hypothesized... 

Indanone was prepared by chlorosulfonation of indane to give both the 4- and 5-positional isomers (2), which are difficult to separate. However, we could aminate the sulfonylchlorides and metallate the activated methylene of the 4-isomer in the mixture to give, upon quenching with oxygen, the indanol S2. This could be easily separated from any other products, in 25% yield from the sulfonamide mixture (Scheme XI). 

Table 3.10). Construction of indanes, indanones, dihydrobenzofurans, and azain-dolines from aryl chloride precursors via intra-molecular p -arylation has also been communicated. ... 

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