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7,10,14-Tri-t-butyl-3-hydroxy-1,8-bisdehydro[14]annulene

โœ Scribed by Yasunobu Onishi; Takeshi Satake; Masahiko Iyoda; Masazumi Nakagawa

Publisher
Elsevier Science
Year
1979
Tongue
French
Weight
149 KB
Volume
20
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

Tri-t-butyl-(B-methoxyethoxy)methoxybisdehydro[lll]annulene has been prepared. Cleavage of the ether linkage to give hydroxyannulene was unsuccessful. Treatment of the methoxy analogue with iodotrimethylsilane yielded iodoketone, which gave anion of hydroxyannulene by the reaction with base. Formation of hydroxyannulene could be confirmed by NMR spectroscopy and reconversion of the anion into the methoxyannulene. In spite of the remarkable development of annulene chemistry, little is known on hydroxyannulene, ') which can be regarded as nonbenzenoid analogue of phenol. Because we have already prepared 7,10,14-tri-t-butyl-3-methoxy-1,8-bisdehydro[l4]annulene (V)? replacement of the methoxyl group by a more easily cleavable group seemed to give a promising precursor for the preparation of hydroxyannulene. Ethynyl hydroxy ester (I)3' was

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