Carbon catalyzed organic reactions: carbon promoted solvolysis of a phosphate ester derived from 1,1′-bi-2-naphthol

Autor:	Richard E. Pincock, Yumiko Hoyano
Rok vydání:	1980
Předmět:	1 1'-Bi-2-naphthol Organic Chemistry chemistry.chemical_element General Chemistry Phosphate Catalysis chemistry.chemical_compound chemistry Organic reaction Organic chemistry Solvolysis Racemization Carbon
Zdroj:	Canadian Journal of Chemistry. 58:134-137
ISSN:	1480-3291 0008-4042
DOI:	10.1139/v80-021
Popis:	Active carbons which catalyze the racemization of 1,1′-binaphthyl are not effective in racemizing the 2,2′-dihydroxyl and the 8,8′-dicarbomethoxyl derivatives of binaphthyl. The 2,2′-binaphthyl methyl phosphate ester derived from optically active 1,1′-bi-2-naphthol undergoes slow thermal racemization at 190 °C (t1/2 100 min, ▵H≠ 26.1 kcal/mol, ▵S≠ −21 cal/mol deg) in triglyme and this racemization rate is also unaffected by active carbon. However, in the hydroxylic solvent 2-(2-ethoxyethoxy)ethanol at 130 °C the rate of solvolysis of the phosphate ester is increased ca. tenfold by carbon blacks or decolorizing carbon at 1 mg/mL concentration. Control experiments show that the acceleration is not due to soluble impurities released by the carbons; heterogeneous catalysis, probably by acidic and/or nucleophilic functional groups on the carbon surfaces, is involved.
Databáze:	OpenAIRE
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