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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| Language: | English |
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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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| collection | DOAJ |
| description | 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. |
| format | Article |
| id | doaj-art-230dbdc79af140d38ff7fad4ef7b3e2f |
| institution | OA Journals |
| issn | 1016-1104 2345-6914 |
| language | English |
| publishDate | 2000-09-01 |
| publisher | University of Tehran |
| record_format | Article |
| series | Journal of Sciences, Islamic Republic of Iran |
| spelling | doaj-art-230dbdc79af140d38ff7fad4ef7b3e2f2025-08-20T02:25:51ZengUniversity of TehranJournal of Sciences, Islamic Republic of Iran1016-11042345-69142000-09-0111331838ADDITION 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-NAPHTHOQUINONESRegioselective 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.https://jsciences.ut.ac.ir/article_31838_3b80911a9bf7e41c93eb5a5fbf28ab6f.pdf |
| spellingShingle | 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 Journal of Sciences, Islamic Republic of Iran |
| title | 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 |
| title_full | 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 |
| title_fullStr | 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 |
| title_full_unstemmed | 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 |
| title_short | 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 |
| title_sort | 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 |
| url | https://jsciences.ut.ac.ir/article_31838_3b80911a9bf7e41c93eb5a5fbf28ab6f.pdf |