Indane, 1-butyl 1-methyl

Alcohol 3 (solid) (1 mmol) and 5% of iodine (0.05 mmol, 12.7 mg) were triturated in a glass mortar for 1 min, transferred to a 15-mL flask and heated at 70 °C for 3 h. an aqueous solution of Na2S203-5H20 (10%, 20 mL) was then poured into the cooled mixture and the crude product was extracted with tert-butyl methyl ether (35 mL) and washed with water. Pure l,l,3-trimethyl-3-phenyl-indane (5, colorless oil) was obtained by column chromatography (Si02, hexane-CH2C12 4 1) in 91% yield. 

Table 19 shows results from the a-acetoxylation of two 2-alkyl-indans under different conditions analogous homogeneous reactions are included for comparison. Table 19 demonstrates that, at most, a weak effect is noticeable in the case of 2-t-butylindan, in that anodic oxidation on platinum, a strongly adsorbing metal, gives a cis/trans ratio that is about 10 times that observed from a 2-t-butyl-1-indanyl cation generated by solvolysis. Ratios on the weaker adsorbing electrode materials, carbon and lead dioxide, fall in between. For a smaller substituent (R = methyl) no effect is observable. 

The signal observed at 5 = 314.2 ppm in the C NMR spectrum is the most deshielded signal ever observed for a carbene center. [27] The carbene 50 is stable for days in solution at -50°C but undergoes a classical C-H insertion reaction at room temperature within a few hours, the 4,6-di-tert-butyl-l,l-dimethyl-3-(methyl-fert-butylamino)indan 51 was obtained as the major product. [65]... 

Oxidative rearrangements, via oxythallation, have been improved in yield and selectivity by the use of thallium(iii) nitrate supported on clay rather than in methanolic solution. Thus, cyclohexene gave an 85% yield of dimethoxymethyl-cyclopentane while 1-tetralone, which normally gives a complex mixture of products, gave a 1 1 mixture of methyl indane-l-carboxylate and 2-methoxytetralone. An efficient, large-scale procedure for the direct cis-dihydroxylation of olefins has been reported. The oxidant is t-butyl hydroperoxide and the catalyst osmium tetroxide, with the reaction conducted under alkaline conditions (E%N OH ), so facilitating a rapid turnover of catalyst via enhanced hydrolysis of the osmate esters. The method appears to be more advantageous for the more substituted olefins than the Hofmann and Miles procedure. 

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