In connection with other work, we desired to demethylate a brcminated aryl methyl ether. which also contained an acid-sensitive group elsewhere in the molecule. The common acidic reagents (1,2) were obviously not applicable and, because Grignard reagents are of limited use in the presence of halog
Reactions with thioethoxide ion in dimethylformamide. I. Selective demethylation of aryl methyl ethers
β Scribed by Feutrill, GI; Mirrington, RN
- Book ID
- 120971217
- Publisher
- Commonwealth Scientific and Industrial Research Organisation Publishing
- Year
- 1972
- Tongue
- English
- Weight
- 561 KB
- Volume
- 25
- Category
- Article
- ISSN
- 0004-9425
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π SIMILAR VOLUMES
In the pursuit of ring-constrained analogues of buprenorphine, we wished to prepare 6-O-demethylated analogues of the thevinols and orvinols. Previously it had been disclosed that lithium aluminum hydride (LAH) in THF containing a chlorinated solvent could achieve this transformation. Here we report
## Abstract The reactivity of the lithium halides in 83.3% pyridineβdimethylformamide changes from Cl^β^ > Br^β^ > I^β^ to Br^β^ > I^β^ to Br^β^ > I^β^ > Cl^β^ with increasing concentration of the salt from 0 to 0.35 M. This behaviour is explained by ion pairing which reduces the concentration of r