Halophenol Rearrangement in Lewis Acid-Catalyzed Friedel–Crafts Conditions: Evidence of Competitive Initial Protonation and Acylation
Halogen rearrangement was observed during the Lewis acid-catalyzed Friedel–Crafts reaction of phthalic anhydride with bromophenols or bromoanisole. Further investigation revealed that 2-, 3-, and 4-bromophenols undergo rearrangement into other isomers under these reaction conditions. Product distrib...
| Main Authors: | , , , , , |
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| Format: | Article |
| Language: | English English |
| Published: |
CSIRO Publishing
2008
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| Online Access: | http://psasir.upm.edu.my/id/eprint/6021/1/Halophenol%20Rearrangement%20in%20Lewis%20Acid.pdf |
| _version_ | 1796967081199009792 |
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| author | Koushik, Saha Lajis, Md Nordin Abas, Faridah Ali Naji, Nabil Hamzah, A. Sazali Shaari, Khozirah |
| author_facet | Koushik, Saha Lajis, Md Nordin Abas, Faridah Ali Naji, Nabil Hamzah, A. Sazali Shaari, Khozirah |
| author_sort | Koushik, Saha |
| collection | UPM |
| description | Halogen rearrangement was observed during the Lewis acid-catalyzed Friedel–Crafts reaction of phthalic anhydride with bromophenols or bromoanisole. Further investigation revealed that 2-, 3-, and 4-bromophenols undergo rearrangement into other isomers under these reaction conditions. Product distribution from these reactions suggested that halogen rearrangement takes place during the s-complex intermediate of the condensation step. Furthermore, iodophenol undergoes hydrodeiodination rapidly rather than rearrangement, whereas chlorophenol does not undergo rearrangement at all.
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| first_indexed | 2024-03-06T07:08:41Z |
| format | Article |
| id | upm.eprints-6021 |
| institution | Universiti Putra Malaysia |
| language | English English |
| last_indexed | 2024-03-06T07:08:41Z |
| publishDate | 2008 |
| publisher | CSIRO Publishing |
| record_format | dspace |
| spelling | upm.eprints-60212015-09-28T07:56:10Z http://psasir.upm.edu.my/id/eprint/6021/ Halophenol Rearrangement in Lewis Acid-Catalyzed Friedel–Crafts Conditions: Evidence of Competitive Initial Protonation and Acylation Koushik, Saha Lajis, Md Nordin Abas, Faridah Ali Naji, Nabil Hamzah, A. Sazali Shaari, Khozirah Halogen rearrangement was observed during the Lewis acid-catalyzed Friedel–Crafts reaction of phthalic anhydride with bromophenols or bromoanisole. Further investigation revealed that 2-, 3-, and 4-bromophenols undergo rearrangement into other isomers under these reaction conditions. Product distribution from these reactions suggested that halogen rearrangement takes place during the s-complex intermediate of the condensation step. Furthermore, iodophenol undergoes hydrodeiodination rapidly rather than rearrangement, whereas chlorophenol does not undergo rearrangement at all. CSIRO Publishing 2008 Article PeerReviewed application/pdf en http://psasir.upm.edu.my/id/eprint/6021/1/Halophenol%20Rearrangement%20in%20Lewis%20Acid.pdf Koushik, Saha and Lajis, Md Nordin and Abas, Faridah and Ali Naji, Nabil and Hamzah, A. Sazali and Shaari, Khozirah (2008) Halophenol Rearrangement in Lewis Acid-Catalyzed Friedel–Crafts Conditions: Evidence of Competitive Initial Protonation and Acylation. Australian Journal of Chemistry, 61 (10). pp. 821-825. ISSN 0004-9425 http://dx.doi.org/10.1071/CH08084 10.1071/CH08084 English |
| spellingShingle | Koushik, Saha Lajis, Md Nordin Abas, Faridah Ali Naji, Nabil Hamzah, A. Sazali Shaari, Khozirah Halophenol Rearrangement in Lewis Acid-Catalyzed Friedel–Crafts Conditions: Evidence of Competitive Initial Protonation and Acylation |
| title | Halophenol Rearrangement in Lewis Acid-Catalyzed Friedel–Crafts Conditions: Evidence of Competitive Initial Protonation and Acylation
|
| title_full | Halophenol Rearrangement in Lewis Acid-Catalyzed Friedel–Crafts Conditions: Evidence of Competitive Initial Protonation and Acylation
|
| title_fullStr | Halophenol Rearrangement in Lewis Acid-Catalyzed Friedel–Crafts Conditions: Evidence of Competitive Initial Protonation and Acylation
|
| title_full_unstemmed | Halophenol Rearrangement in Lewis Acid-Catalyzed Friedel–Crafts Conditions: Evidence of Competitive Initial Protonation and Acylation
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| title_short | Halophenol Rearrangement in Lewis Acid-Catalyzed Friedel–Crafts Conditions: Evidence of Competitive Initial Protonation and Acylation
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| title_sort | halophenol rearrangement in lewis acid catalyzed friedel crafts conditions evidence of competitive initial protonation and acylation |
| url | http://psasir.upm.edu.my/id/eprint/6021/1/Halophenol%20Rearrangement%20in%20Lewis%20Acid.pdf |
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