Umpolung of tropone: The synthesis of novel 2-substituted tropones via 2-halocycloheptadienone enolates
β Scribed by Hiroyuki Miyano; Makoto Nitta
- Book ID
- 104216697
- Publisher
- Elsevier Science
- Year
- 1988
- Tongue
- French
- Weight
- 255 KB
- Volume
- 29
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
2-Halocycloheptadienone enolates, 7
which were generated by the reaction of 2-halotropones with hydride, Grignard, and organolithium reagents, reacted with cationic electrophiles including tropylium ion to give 2-substituted tropone derivatives.
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## Abstract Acidβcatalysed decomposition of tropyl ether gives tropone and cycloheptatriene in 83.5 and 90 % yields, respectively. Chlorination of tropone in carbon tetrachloride solution yields tropone dichloride, which can be made to isomerize to the hydrochloride of 2βchlorotropone; 2βchlorotro
Received in Japan 2 March 1970; received in UK for publication 31 firoh 1970) The first synthesis of a 2,3-homotropone was carried out by Pettit et al 1) from cyclooctatetraene via several steps. In this communication we would like to report a