Substituent Effects on Regioselectivity of the Diels-Alder Reactions: Reactions of 10-Allyl-1,8-dichloroanthracene with 2-Chloroacrylonitrile, 1-Cyanovinyl Acetate and Phenyl Vinyl Sulfone
Diels-Alder reaction of 10-allyl-1,8-dichloroanthracene (3) with 2-chloroacrylonitrile (4) and 1-cyanovinyl acetate (5) gives exclusively the ortho isomer while its reaction with phenyl vinyl sulfone (10) yields a mixture of two isomeric adducts with priority to ortho isomer. The reactions proceeded...
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| Language: | English |
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Wiley
2016-01-01
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| Series: | Journal of Chemistry |
| Online Access: | http://dx.doi.org/10.1155/2016/3943060 |
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| author | Mujeeb A. Sultan Usama Karama |
| author_facet | Mujeeb A. Sultan Usama Karama |
| author_sort | Mujeeb A. Sultan |
| collection | DOAJ |
| description | Diels-Alder reaction of 10-allyl-1,8-dichloroanthracene (3) with 2-chloroacrylonitrile (4) and 1-cyanovinyl acetate (5) gives exclusively the ortho isomer while its reaction with phenyl vinyl sulfone (10) yields a mixture of two isomeric adducts with priority to ortho isomer. The reactions proceeded under microwave condition in xylene. Configurations of these isomers have been assigned with the help of NMR spectra. The results indicated that the steric effect is dominating toward the isomer regioselectivity in the Diels-Alder reaction of the present compounds. |
| format | Article |
| id | doaj-art-1fb785d129a64e9cb73beb015ab051ac |
| institution | Kabale University |
| issn | 2090-9063 2090-9071 |
| language | English |
| publishDate | 2016-01-01 |
| publisher | Wiley |
| record_format | Article |
| series | Journal of Chemistry |
| spelling | doaj-art-1fb785d129a64e9cb73beb015ab051ac2025-02-03T01:24:20ZengWileyJournal of Chemistry2090-90632090-90712016-01-01201610.1155/2016/39430603943060Substituent Effects on Regioselectivity of the Diels-Alder Reactions: Reactions of 10-Allyl-1,8-dichloroanthracene with 2-Chloroacrylonitrile, 1-Cyanovinyl Acetate and Phenyl Vinyl SulfoneMujeeb A. Sultan0Usama Karama1Chemistry Department, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi ArabiaChemistry Department, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi ArabiaDiels-Alder reaction of 10-allyl-1,8-dichloroanthracene (3) with 2-chloroacrylonitrile (4) and 1-cyanovinyl acetate (5) gives exclusively the ortho isomer while its reaction with phenyl vinyl sulfone (10) yields a mixture of two isomeric adducts with priority to ortho isomer. The reactions proceeded under microwave condition in xylene. Configurations of these isomers have been assigned with the help of NMR spectra. The results indicated that the steric effect is dominating toward the isomer regioselectivity in the Diels-Alder reaction of the present compounds.http://dx.doi.org/10.1155/2016/3943060 |
| spellingShingle | Mujeeb A. Sultan Usama Karama Substituent Effects on Regioselectivity of the Diels-Alder Reactions: Reactions of 10-Allyl-1,8-dichloroanthracene with 2-Chloroacrylonitrile, 1-Cyanovinyl Acetate and Phenyl Vinyl Sulfone Journal of Chemistry |
| title | Substituent Effects on Regioselectivity of the Diels-Alder Reactions: Reactions of 10-Allyl-1,8-dichloroanthracene with 2-Chloroacrylonitrile, 1-Cyanovinyl Acetate and Phenyl Vinyl Sulfone |
| title_full | Substituent Effects on Regioselectivity of the Diels-Alder Reactions: Reactions of 10-Allyl-1,8-dichloroanthracene with 2-Chloroacrylonitrile, 1-Cyanovinyl Acetate and Phenyl Vinyl Sulfone |
| title_fullStr | Substituent Effects on Regioselectivity of the Diels-Alder Reactions: Reactions of 10-Allyl-1,8-dichloroanthracene with 2-Chloroacrylonitrile, 1-Cyanovinyl Acetate and Phenyl Vinyl Sulfone |
| title_full_unstemmed | Substituent Effects on Regioselectivity of the Diels-Alder Reactions: Reactions of 10-Allyl-1,8-dichloroanthracene with 2-Chloroacrylonitrile, 1-Cyanovinyl Acetate and Phenyl Vinyl Sulfone |
| title_short | Substituent Effects on Regioselectivity of the Diels-Alder Reactions: Reactions of 10-Allyl-1,8-dichloroanthracene with 2-Chloroacrylonitrile, 1-Cyanovinyl Acetate and Phenyl Vinyl Sulfone |
| title_sort | substituent effects on regioselectivity of the diels alder reactions reactions of 10 allyl 1 8 dichloroanthracene with 2 chloroacrylonitrile 1 cyanovinyl acetate and phenyl vinyl sulfone |
| url | http://dx.doi.org/10.1155/2016/3943060 |
| work_keys_str_mv | AT mujeebasultan substituenteffectsonregioselectivityofthedielsalderreactionsreactionsof10allyl18dichloroanthracenewith2chloroacrylonitrile1cyanovinylacetateandphenylvinylsulfone AT usamakarama substituenteffectsonregioselectivityofthedielsalderreactionsreactionsof10allyl18dichloroanthracenewith2chloroacrylonitrile1cyanovinylacetateandphenylvinylsulfone |