Chlorination of phenylallene derivatives with 1-chloro-1,2-benziodoxol-3-one: synthesis of vicinal-dichlorides and chlorodienes
Allyl and vinyl chlorides represent important structural motifs in organic chemistry. Herein is described the chemoselective and regioselective reaction of aryl- and α-substituted phenylallenes with the hypervalent iodine (HVI) reagent 1-chloro-1,2-benziodoxol-3-one. The reaction typically results i...
| Main Authors: | , |
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2018-04-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.14.67 |
| _version_ | 1818619620350754816 |
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| author | Zhensheng Zhao Graham K. Murphy |
| author_facet | Zhensheng Zhao Graham K. Murphy |
| author_sort | Zhensheng Zhao |
| collection | DOAJ |
| description | Allyl and vinyl chlorides represent important structural motifs in organic chemistry. Herein is described the chemoselective and regioselective reaction of aryl- and α-substituted phenylallenes with the hypervalent iodine (HVI) reagent 1-chloro-1,2-benziodoxol-3-one. The reaction typically results in vicinal dichlorides, except with proton-containing α-alkyl substituents, which instead give chlorinated dienes as the major product. Experimental evidence suggests that a radical mechanism is involved. |
| first_indexed | 2024-12-16T17:40:23Z |
| format | Article |
| id | doaj.art-6286b2c7d6a441a5a605383914191a11 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-16T17:40:23Z |
| publishDate | 2018-04-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-6286b2c7d6a441a5a605383914191a112022-12-21T22:22:37ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972018-04-0114179680210.3762/bjoc.14.671860-5397-14-67Chlorination of phenylallene derivatives with 1-chloro-1,2-benziodoxol-3-one: synthesis of vicinal-dichlorides and chlorodienesZhensheng Zhao0Graham K. Murphy1Department of Chemistry, University of Waterloo, 200 University Ave. W., Waterloo, N2L3G1, ON, CanadaDepartment of Chemistry, University of Waterloo, 200 University Ave. W., Waterloo, N2L3G1, ON, CanadaAllyl and vinyl chlorides represent important structural motifs in organic chemistry. Herein is described the chemoselective and regioselective reaction of aryl- and α-substituted phenylallenes with the hypervalent iodine (HVI) reagent 1-chloro-1,2-benziodoxol-3-one. The reaction typically results in vicinal dichlorides, except with proton-containing α-alkyl substituents, which instead give chlorinated dienes as the major product. Experimental evidence suggests that a radical mechanism is involved.https://doi.org/10.3762/bjoc.14.67allenechlorinationhypervalent iodinesynthetic methodsvinyl chloride |
| spellingShingle | Zhensheng Zhao Graham K. Murphy Chlorination of phenylallene derivatives with 1-chloro-1,2-benziodoxol-3-one: synthesis of vicinal-dichlorides and chlorodienes Beilstein Journal of Organic Chemistry allene chlorination hypervalent iodine synthetic methods vinyl chloride |
| title | Chlorination of phenylallene derivatives with 1-chloro-1,2-benziodoxol-3-one: synthesis of vicinal-dichlorides and chlorodienes |
| title_full | Chlorination of phenylallene derivatives with 1-chloro-1,2-benziodoxol-3-one: synthesis of vicinal-dichlorides and chlorodienes |
| title_fullStr | Chlorination of phenylallene derivatives with 1-chloro-1,2-benziodoxol-3-one: synthesis of vicinal-dichlorides and chlorodienes |
| title_full_unstemmed | Chlorination of phenylallene derivatives with 1-chloro-1,2-benziodoxol-3-one: synthesis of vicinal-dichlorides and chlorodienes |
| title_short | Chlorination of phenylallene derivatives with 1-chloro-1,2-benziodoxol-3-one: synthesis of vicinal-dichlorides and chlorodienes |
| title_sort | chlorination of phenylallene derivatives with 1 chloro 1 2 benziodoxol 3 one synthesis of vicinal dichlorides and chlorodienes |
| topic | allene chlorination hypervalent iodine synthetic methods vinyl chloride |
| url | https://doi.org/10.3762/bjoc.14.67 |
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