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Synthesis and properties of benzo[c]-7,10,14-tri-t-butyl-1,8-didehydro[14]annulene

โœ Scribed by Akio Yasuhara; Takeshi Satake; Masahiko Iyoda; Masazumi Nakagawa

Publisher
Elsevier Science
Year
1975
Tongue
French
Weight
211 KB
Volume
16
Category
Article
ISSN
0040-4039

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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. Formati

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Sumnary: Tri-t-butylcarboxybisdehydro[lrl]annulene was converted by the Curtius reactiog into unstable aminoannulene, which could be characterized as N-acetyl derivative. The pKa-value of the aminoannulene reflects aromatic nature of the annulene nucleus. Aminoannulenes are interesting compounds bei

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## Suppression of diatropicity of 1,8-bisdehydroil41 annulene by annelation with a benzene (1) was found to be larger than the case of fusion with a naphthalone nucleus (2). In view of the fact that annelation of 1,8-bisdehydro[l&]annulene with two naphthalene nuclei at the positions which make p

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3-Acetyl and 3-carboxy derivatives of 7,10,14-tri-t-butyl-1,8-bisdehydro[14]-annulene and the pKโ€ฒa-value of the latter compound
โœ Takeshi Satake; Shin'ichi Nakatsuji; Masahiko Iyoda; Shuzo Akiyama; Masazumi Nak ๐Ÿ“‚ Article ๐Ÿ“… 1976 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 252 KB

Received in Japan 31 March 1976; received in UK for Prlblication University 16 April 19'7hj Formation of 3-substituted derivatives by various substitution reactions of 1,8-bisdehydroi14]annulene (1) suggests that the most reactive sites in the bis-dehydroil41 annulene ring are the positions adjacen