The Directed Lithiation of Benzenoid Aromatic Systems
β Scribed by Andrew E. H. Wheatley
- Publisher
- John Wiley and Sons
- Year
- 2003
- Weight
- 48 KB
- Volume
- 34
- Category
- Article
- ISSN
- 0931-7597
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π SIMILAR VOLUMES
The dimethylacetal of benzaldehyde and some 3, 3,4 and 3,4,5 oxygenated derivatives thereof are regiospecifically deprotonated at the 2-position by alkyl lithiums. The resulting aryl lithiums provide various 2-substituted benzaldehydes in moderate to excellent yields. Following the pioneering work
3-Acylchromone acetals are lithiated at C-2. Subsequent electrophilic trapping gives chtomones 4 together with a ting-conwacted rimer 6. During the formation of some acetals, an acidcatalysed rearrangement to a 2-substituted 3-fotmylchromone acetal is observed.