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
7,10,14-Tri-t-butyl-3-amino-1,8-bisdehydro[14]annulene
โ Scribed by Takeshi Satake; Yasunobu Onishi; Masahiko Iyoda; Masazumi Nakagawa
- Publisher
- Elsevier Science
- Year
- 1979
- Tongue
- French
- Weight
- 143 KB
- Volume
- 20
- Category
- Article
- ISSN
- 0040-4039
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โฆ Synopsis
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 being formal counterpart of aniline. However, little is known hitherto on amino derivative of annulene!'2) Because we have previously prepared 7,10,14-tri-t-butyl-3-carboxy-1,8-bisdehydro[14]annulene
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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
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
1,8-Didehydro[l&]annulene (XII) is an unusually stable and highly aromatic annulene prepared and extensively investigated by F. Sondheimer and his coworkers (1). The dienyne ketones (II and IX) obtained from enyne aldehydes (I and VIII), key intermediates in the syntheses of tetrasubstituted tetrade