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https://locus.ufv.br//handle/123456789/24979
Tipo: | Artigo |
Título: | Síntese de novas fitotoxinas derivadas do 8- oxabiciclo[ 3. 2. 1] oct- 6- en- 3- ona |
Autor(es): | Barbosa, Luiz C. A. Maltha, Célia R. A. Demuner, Antônio J. Ganen, Flávia R. Silva, Antônio A. da |
Abstract: | The [4+3] cycloaddition was utilized in order to prepare 8-oxabicyclo[3.2.1]oct-6-en-3-one (1) derivatives. The correspondent acetonide 6 was converted into several alcohols (11-16). Addition of aryllithium reagents to 6 resulted in 3-(2-fluorophenyl)-6,7-exo-isopropylidenedioxy -8-oxabicyclo[3.2.1]octan-3a-ol (11, 72%) and 3-(2,4-dimethoxyphenyl)-6,7-exo-isopropylidenedioxy-8-oxabicyclo[3.2.1]octan -3a-ol (16, 20%). The 3-butyl-6,7-exo-isopropylidenedioxy-8-oxabicyclo[3.2.1]octan-3 a-ol (15, 56%) was obtained through a Grignard reaction. Reduction of 6 resulted in 6,7-exo-isopropylidenedioxy-8-oxabicyclo[3.2.1]octan-3 b-ol (7, 62%) and 6,7-exo-isopropylidenedioxy-8-oxabicyclo[3.2.1]octan-3 a-ol (8, 20%). The alcohols were treated with thionyl chloride in pyridine, and the corresponding alkenes were obtained with 31-80% yield. The effect of these compounds on the development of radicle and aerial parts of Sorghum bicolor was evaluated. |
Palavras-chave: | [ 4+ 3] cycloaddition Oxyallyl cations Herbicides |
Editor: | Química Nova |
Tipo de Acesso: | Open Access |
URI: | http://dx.doi.org/10.1590/S0100-40422005000300015 http://www.locus.ufv.br/handle/123456789/24979 |
Data do documento: | Mai-2005 |
Aparece nas coleções: | Artigos |
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artigo.pdf | texto completo | 259,92 kB | Adobe PDF | Visualizar/Abrir |
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