Unusual reactions of guaiazulene with N-bromosuccinimide and synthesis of variously functionalized azulenes using these reactions

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Title:Unusual reactions of guaiazulene with N-bromosuccinimide and synthesis of variously functionalized azulenes using these reactions
Creators:
Nozoe, Tetsuo
Shindo, Kimio
Wakabayashi, Hidetsugu
Kurihara, Teruo
Ishikawa, Sumio
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 56, 5, pp. 991-1010

Abstract

Treatment of guaiazulene (<i>Ia</i>) with NBS in benzene gives various, side-chain-brominated compounds, but in hexane it affords exclusively 3-bromoguaiazulene (<i>Id</i>). Compound <i>Id</i> is stable in hexane at 5°C in the absence of oxygen, whereas in benzene it changes very rapidly to a mixture of similar compounds as those directly obtained from <i>Ia</i> and NBS in benzene. Possible pathways for the formation of these compounds are briefly discussed. By utilizing these reactions, various kinds of side-chain functionalized azulenes that are otherwise not available by conventional methods can be readily prepared from <i>Ia</i>.

Title:Unusual reactions of guaiazulene with N-bromosuccinimide and synthesis of variously functionalized azulenes using these reactions
Creators:
Nozoe, Tetsuo
Shindo, Kimio
Wakabayashi, Hidetsugu
Kurihara, Teruo
Ishikawa, Sumio
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:56
Number:5
Page Range:pp. 991-1010
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19910991UNSPECIFIED
ID Code:5017
Item Type:Article
Deposited On:22 Feb 2010 11:28
Last Modified:22 Feb 2010 10:29

Citation

Nozoe, Tetsuo; Shindo, Kimio; Wakabayashi, Hidetsugu; Kurihara, Teruo; Ishikawa, Sumio (1991) Unusual reactions of guaiazulene with N-bromosuccinimide and synthesis of variously functionalized azulenes using these reactions. Collection of Czechoslovak Chemical Communications, 56 (5). pp. 991-1010. ISSN 0010-0765

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