Synthesis of naphthalenes using acid-catalyzed ring-opening and recyclization of 3-acetyl-5,5-diaryl-2-methyl-4,5-dihydrofurans. Isolation of intermediates
S. Kajikawa et al., Synthesis of naphthalenes using acid-catalyzed ring-opening and recyclization of 3-acetyl-5,5-diaryl-2-methyl-4,5-dihydrofurans. Isolation of intermediates, TETRAHEDR L, 42(19), 2001, pp. 3351-3354
3-Acetyl-5,5-diaryl-2-methyl-4,5-dihydrofurans were heated in concentrated
hydrochloric acid to give the 4-aryl-1-methylnaphthalenes in high yields. T
he same reaction was carried out in hydrochloric acid diluted with acetonit
rile to give the 5,5-diaryl-4-penten-2-ones (87-96%), while treatment of th
e dihydrofurans with p-toluenesulfonic acid in acetonitrile afforded the 3-
(2,2-diarylethenyl)-4-hydroxy-3-penten-2-ones (73-91%) which were transform
ed in diluted hydrochloric acid into the 5,5-diaryl-4-penten-2-ones. It was
demonstrated that the 3- and 4-penten-2-ones were intermediates of the 3-a
ryl-1-methylnaphthalenes since the 3- and 4-penten-2-ones were easily conve
rted into the corresponding naphthalenes in concentrated hydrochloric acid.
The UV irradiation of the dihydrofurans in the presence of hydrochloric ac
id quantitatively gave the 2-acetyl-4-aryl-1methylnaphthalenes (94-97%) via
the same 3-penten-2-one intermediates. (C) 2001 Elsevier Science Ltd. Al]
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