Aryl pinacols and epoxides, respectively, are cleanly
and in high yield converted via superacidic
dehydrative cyclization to the corresponding condensed aromatics.
Dehydrative cyclization of
benzopinacol (1a), triphenylacetophenone (2), and
tetraphenylethylene oxide (9) give 9,10-diphenylphenanthrene (3a) as the major product in acidic
media stronger than H
o = −11.
Aryl
pinacol 12a forms the condensed aromatic 13a as
the major product in acidic media stronger than
H
o = −13.5. It is proposed that the
dehydrative cyclizations to provide aromatics 3a and
13a occurs
through dicationic intermediates. Substituted benzopinacols
1f, 1g, and 1j are prepared and
give
the corresponding phenanthrenes (3f, 3g, and
3j) in high yields. The regiochemistry of
the
cyclization of substituted benzopinacols is controlled by deactivating
substituents on the aryl rings.
Aryl pinacols (12a−d) derived from
acenaphthenequinone and pinacol 15 also give
condensed
aromatics (13a−d and 16, repectively) with
superacidic triflic acid.
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