Improved Synthesis of 1,4-Phenanthrenequinones from Diels-Alder Cycloadditions of 2-(p-Tolylsulfinyl)-1,4-benzoquinone. -A variety of substituted 1,4-phenanthrenequinone compounds is prepared. In most cases application of the high pressure variant is more effective. Styrenes (VI), under thermal cond
Improved Synthesis of 1,4-Phenanthrenequinones from Diels-Alder Cycloadditions of 2-(p-Tolylsulfinyl)-1,4-benzoquinone
✍ Scribed by M.Carmen Carreño*; Jesús Mahugo; Antonio Urbano
- Publisher
- Elsevier Science
- Year
- 1997
- Tongue
- French
- Weight
- 589 KB
- Volume
- 38
- Category
- Article
- ISSN
- 0040-4039
No coin nor oath required. For personal study only.
✦ Synopsis
A wide range of substituted 1,4-phenanthrenequinones 5a-g and benz[c]-and benz[a]-l,4pbenantbrenequinones (5h)and (5i) were syntbezisedin one step tbroughDieIs-Aldercycloadditions of 2-(p-tolylsulfinyl)-1,4-benzoquinone2 and vinylaromaticderivatives la-i under thermal and higb pressureconditionsin moderateto goodyields(33-80%).0 1997Elsevier Science Ltd.
📜 SIMILAR VOLUMES
Enantiopure sulfinylquinones (+)-2 and (+)-3 reacted with Dane's diene 1 under thermal and ZnBr 2 Lewis acid conditions with reversal regiochemistry but similar ~-facial diastereoselectivity to afford, after spontaneous elimination of the sulfinyl group, tetracyclic derivatives 4-9.