119367-63-4Relevant articles and documents
Lithium 2-(2-lithiomethylphenyl)ethanolate from isochroman: Easy preparation of substituted benzoxepines and functionalised arenes
Almena, Juan,Foubelo, Francisco,Yus, Miguel
, p. 3365 - 3374 (2007/10/02)
The reaction of isochroman (1) with an excess of lithium powder and a catalytic amount of DTBB (2.5 mol %) in THF at 20°C yields the title intermediate, which by reaction with different electrophiles (H2O, D2O, CO2 and carbonyl compounds) at temperatures ranging between -78 and 20°C yields, after hydrolysis, the corresponding products 3. Diols 3h-m, derived from benzaldehyde or ketones, give upon treatment with 85% phosphoric acid the corresponding benzoxepines 5h-m. In the other cases, Friedel-Crafts products resulting from a rearrangement of the first carbenium ion formed, are obtained.