Synthesis of some fenchyl-substituted alkenes and enol-ethers containing 3-oxyphenyl substituents by the Barton-Kellogg reaction

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]

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

• 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 - Síntese e aplicação de derivados de pigmentos de flores
• Beneficiário: Erick Leite Bastos
• Modalidade de apoio: Auxílio à Pesquisa - Jovens Pesquisadores