| Texto completo | |
| Autor(es): |
Ciscato, Luiz Francisco M. L.
[1, 2]
;
Bastos, Erick L.
[3]
;
Bartoloni, Fernando H.
[1]
;
Guenther, Wolfgang
[2]
;
Weiss, Dieter
[2]
;
Beckert, Rainer
[2]
;
Baader, Wilhelm Josef
[1]
Número total de Autores: 7
|
| Afiliação do(s) autor(es): | [1] Univ Sao Paulo, Inst Quim, Dept Quim Fundamental, BR-05508000 Sao Paulo - Brazil
[2] Univ Jena, Inst Organ Chem & Makromol Chem, D-07737 Jena - Germany
[3] Univ Fed ABC, Ctr Ciencias Nat & Humanas, BR-09210170 Santo Andre, SP - Brazil
Número total de Afiliações: 3
|
| Tipo de documento: | Artigo Científico |
| Fonte: | Journal of the Brazilian Chemical Society; v. 21, n. 10, p. 1896-1904, 2010. |
| Citações Web of Science: | 5 |
| Resumo | |
The synthesis of one fenchyl-substituted alkene and two enol-ethers, containing 3-oxyphenyl substituents by the Barton-Kellogg reaction is described. The tri-substituted aromatic fenchyl-alkene 1a was prepared in 53% yield from thiofenchone and a diazoanisole; whereas enol-ethers 1b and 1c were obtained (95 and 75% yield, respectively) using an inverse approach based on diazofenchone and aromatic thionoesters. A mixture of Z and E isomers was obtained in all cases; isomer attribution and quantification has been carried out by analysis of NMR spectroscopic data assisted by theoretical calculations (E/Z ratio: 1a = 0.72, 1b = 2.2, 1c = 1.8). Reaction proceeds with low stereoselectivity leading to the preferential formation of diastereoisomeric olefins and enol-ethers where the aromatic substituent resides at the side of the two fenchyl methyl groups. (AU) | |
| Processo FAPESP: | 06/03420-7 - Estudos sobre o mecanismo da decomposicao induzida de 1,2-dioxetanos e da reacao peroxi-oxalato; aplicacoes da quimiluminescencia do luminol. |
| Beneficiário: | Joséf Wilhelm Baader |
| Modalidade de apoio: | Auxílio à Pesquisa - Regular |
| Processo FAPESP: | 05/58320-4 - Efeito da estrutura e do meio de reação sobre a quimiluminescência de dioxetanonas |
| Beneficiário: | Fernando Heering Bartoloni |
| Modalidade de apoio: | Bolsas no Brasil - Doutorado Direto |
| Processo FAPESP: | 07/00684-6 - Sintese e aplicacao de derivados de pimentos de flores. |
| Beneficiário: | Erick Leite Bastos |
| Modalidade de apoio: | Auxílio à Pesquisa - Jovens Pesquisadores |