ADDITION OF UNSYMMETRICAL DIENES TO ACYL-1,4-BENZOQUINONES AND OXIDATION OF THE ADDUCTS WITH MANGANESE DIOXIDE: A REGIOSPECIFIC ROUTE TO MONO- AND DI-METHYL-1,4-NAPHTHOQUINONES
Regioselective Diels-Alder reactions of acyl-1,4-benzoquinones 1 with, severally, isoprene, trans-piperylene,1-acetoxy-1,3-butadiene and 1-methoxy-1,3-butadiene gave the corresponding adducts 2 in high yield. Treatment of the adducts 2 with manganese dioxide gave regiospecifically the corresponding...
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| Format: | Article |
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| Language: | English |
| Published: |
University of Tehran
2000-09-01
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| Series: | Journal of Sciences, Islamic Republic of Iran |
| Online Access: | https://jsciences.ut.ac.ir/article_31838_3b80911a9bf7e41c93eb5a5fbf28ab6f.pdf |
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| Summary: | Regioselective Diels-Alder reactions of acyl-1,4-benzoquinones 1 with, severally, isoprene, trans-piperylene,1-acetoxy-1,3-butadiene and 1-methoxy-1,3-butadiene gave the corresponding adducts 2 in high yield. Treatment of the adducts 2 with manganese dioxide gave regiospecifically the corresponding 1,4-naphthoquinones 3. In several cases, the adducts of the acetylquinones afforded intermediates of type 4, which subsequently gave the corresponding naphthoquinones by de-acetylation and aromatization. |
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| ISSN: | 1016-1104 2345-6914 |