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Access to 'Friedel-Crafts-restricted' tert-alkyl aromatics by activation/methylation of tertiary benzylic alcohols
- Source :
- The Journal of organic chemistry. 77(7)
- Publication Year :
- 2012
-
Abstract
- Herein we describe a two-step protocol to prepare m-tert-alkylbenzenes. The appropriate tertiary benzylic alcohols are activated with SOCl(2) or concentrated HCl and then treated with trimethylaluminum, affording the desired products in 68-97% yields (22 examples). This reaction sequence is successful in the presence of a variety of functional groups, including acid-sensitive and Lewis-basic groups. In addition to t-Bu groups, 1,1-dimethylpropyl and 1-ethyl-1-methylpropyl groups can also be installed using this method.
Details
- ISSN :
- 15206904
- Volume :
- 77
- Issue :
- 7
- Database :
- OpenAIRE
- Journal :
- The Journal of organic chemistry
- Accession number :
- edsair.doi.dedup.....d8a95381a2ae0d43389b942fba84e5c7