79991-07-4Relevant articles and documents
Modern Friedel-Crafts Chemistry. Part-XVII. Studies on the Acid-catalysed Dehydration of 3-(α-Naphthylmethyl)-3-pentanol, 2-(α-Naphthyl)-1,1-diphenyl-1-ethanol and 2-Methyl-2-(α-naphthyl)-2-butanol
Khalaf, Ali Ali,Makki, Mohamad S. I. Tawfik,Kaddah, Ahmed M.
, p. 260 - 264 (2007/10/02)
The title α-napthylalkanols were prepared by unequivocal methods and their dehydration patter was examined in the presence of both Lewis and Broensted-Lowry acid-catalysts. 3-(α-Naphthylmethyl)-3-pentanol (5) gave acyclidehydration mixture of 1,1-diethylacenaphthene (10, mainly) and 2-ethyl-1-methyl-2,3-dihydrophenalene (11) with AlCl3/CH3NO2 and an acyclidehydration mixture of 2-methyl-1-(α-naphthyl)-1-butene (12) and Z- and E-3-(α-naphthylmethyl)-2-pentene (13) with 85percent H2SO4, PPA or NaHSO4. 2-(α-Naphthyl)-1,1-diphenyl-1-ethanol (6) gave 1-(α-naphthyl)-2,2-diphenylethene (16) with H2SO4, PPA, NaHSO4 but a different unidentified product with AlCl3/CH3NO2.Finally, 3-methyl-2-(α-naphthyl)-2-butanol (7) gave 1,1,2-trimethyl-acenaphthene (18) with AlCl3/CH3NO2 but 2-methyl-3-(α-naphthyl)-2-butene (19) with 85percent H2SO4 or NaHSO4.Both reactants and products were characterised by elemental, spectral, chemical and glpc analysis.Mechanistic interpretations have been given in terms of carbocation reactions and rearrangements.
