One-pot Selective Formylation and Claisen Rearrangement on Calix[4]arenes
A versatile synthon with formyl and allyl groups at the upper rim of calix[4]arene has been synthesized in two steps. Selective formylation of 25,27-diallyloxy-26,28-dihydroxycalix[4]arene, along with the Claisen rearrangement of the allyl groups, was achieved by reaction with hexamethylenetetraamin...
| Main Authors: | , , , , |
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| Format: | Journal Article |
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Taylor and Francis Ltd
2006
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| Online Access: | http://hdl.handle.net/20.500.11937/7153 |
| _version_ | 1848745284179329024 |
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| author | Mocerino, Mauro Ogden, Mark Pettersen, Jade Skelton, B. White, A. |
| author_facet | Mocerino, Mauro Ogden, Mark Pettersen, Jade Skelton, B. White, A. |
| author_sort | Mocerino, Mauro |
| building | Curtin Institutional Repository |
| collection | Online Access |
| description | A versatile synthon with formyl and allyl groups at the upper rim of calix[4]arene has been synthesized in two steps. Selective formylation of 25,27-diallyloxy-26,28-dihydroxycalix[4]arene, along with the Claisen rearrangement of the allyl groups, was achieved by reaction with hexamethylenetetraamine (hexamine) in glacial acetic acid. A control reaction of the dipropyl analogue shows that the selective formylation takes place independently of the Claisen rearrangement. The crystal structure of the dimethylacetal derivative of 5,17-diformyl-11,23-diallylcalix[4]arene is reported. |
| first_indexed | 2025-11-14T06:14:55Z |
| format | Journal Article |
| id | curtin-20.500.11937-7153 |
| institution | Curtin University Malaysia |
| institution_category | Local University |
| last_indexed | 2025-11-14T06:14:55Z |
| publishDate | 2006 |
| publisher | Taylor and Francis Ltd |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | curtin-20.500.11937-71532019-02-19T05:35:28Z One-pot Selective Formylation and Claisen Rearrangement on Calix[4]arenes Mocerino, Mauro Ogden, Mark Pettersen, Jade Skelton, B. White, A. Claisen rearrangement Calixarenes Formylation A versatile synthon with formyl and allyl groups at the upper rim of calix[4]arene has been synthesized in two steps. Selective formylation of 25,27-diallyloxy-26,28-dihydroxycalix[4]arene, along with the Claisen rearrangement of the allyl groups, was achieved by reaction with hexamethylenetetraamine (hexamine) in glacial acetic acid. A control reaction of the dipropyl analogue shows that the selective formylation takes place independently of the Claisen rearrangement. The crystal structure of the dimethylacetal derivative of 5,17-diformyl-11,23-diallylcalix[4]arene is reported. 2006 Journal Article http://hdl.handle.net/20.500.11937/7153 10.1080/10610270500419072 Taylor and Francis Ltd fulltext |
| spellingShingle | Claisen rearrangement Calixarenes Formylation Mocerino, Mauro Ogden, Mark Pettersen, Jade Skelton, B. White, A. One-pot Selective Formylation and Claisen Rearrangement on Calix[4]arenes |
| title | One-pot Selective Formylation and Claisen Rearrangement on Calix[4]arenes |
| title_full | One-pot Selective Formylation and Claisen Rearrangement on Calix[4]arenes |
| title_fullStr | One-pot Selective Formylation and Claisen Rearrangement on Calix[4]arenes |
| title_full_unstemmed | One-pot Selective Formylation and Claisen Rearrangement on Calix[4]arenes |
| title_short | One-pot Selective Formylation and Claisen Rearrangement on Calix[4]arenes |
| title_sort | one-pot selective formylation and claisen rearrangement on calix[4]arenes |
| topic | Claisen rearrangement Calixarenes Formylation |
| url | http://hdl.handle.net/20.500.11937/7153 |