- 作者: 廖俊臣; 林和盛
- 作者服務機構: Department of Chemistry, National Tsing Hua University, Hsinchu, Taiwan 300
- 中文摘要:
The title compound , a masked 3,6-di-n-propyl-o-benzoquinone, was synthesized from 3,6-di-n-propylcatechol in 82% yield. Its Diels-Alder reaction with methyl propiolate, phenylacetylene, 1-octyne, dimethyl acetylenedicarboxylate, diphenylacetylene and 3-hexyne were studied. The yields of the adducts were excellent except for the last two cases in which the unimolecular decomposition of the title compound to generate 3,6-di-n-propylcatechol methylene ether predominates.
The regiochemistry of the adducts derived from monosubstituted acetylenes were determined by the correlation of 13C chemical shifts of the adducts and the corresponding bicycle[2.2.2]octa-5,7-diene-2,3-diones obtained from the hydrolysis of the spirolactone aromatic compounds in high yields. These synthetic sequences provide an effective entry to bicycle[2.2.2]octa-5,7-diene-2,3-diones and polysubstituted benzene derivatives. - 英文摘要: --
- 中文關鍵字: Diels-Alder Reactions; Masked o-Benzoquinone; Alkynes; Photolysis; Bicyclo[2. 2. 2]octa-5, 7-diene-2, 3-diones.
- 英文關鍵字: Diels-Alder Reactions; Masked o-Benzoquinone; Alkynes; Photolysis; Bicyclo[2. 2. 2]octa-5, 7-diene-2, 3-diones.