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...
| Published in: | Australian Journal of Chemistry |
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| Main Author: | |
| Format: | Article |
| Language: | English |
| Published: |
2008
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| Online Access: | https://www.scopus.com/inward/record.uri?eid=2-s2.0-53849129584&doi=10.1071%2fCH08084&partnerID=40&md5=9d8786e8a067297b8d4340068539d580 |
| Summary: | 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 2008. |
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| ISSN: | 00049425 |
| DOI: | 10.1071/CH08084 |