164731-37-7Relevant articles and documents
1,2-Di(lithiomethyl)benzene from Phthalan: Sequential Introduction of Two Different Electrophiles
Almena, Juan,Foubelo, Francisco,Yus, Miguel
, p. 3351 - 3364 (1995)
The reaction of phthalan (1) with an excess of lithium powder and a catalytic amount of DTBB (2.5 mol percent) in THF at 20 deg C followed by treatment with electrophiles (D2O, CO2 and carbonyl compounds) at -78 deg C leads, after hydrolysis, to the corresponding functionalised benzylic alcohols 3a-g.When the lithiation reaction is continued, after the reaction with the first electrophile, and a second electrophile (H2O, D2O and carbonyl compounds) is added, the corresponding disubstituted compounds 6a-q are prepared.Diols 3c-g and 6h,i,l,n and hydroxyacids 6a,c,f,k are easily dehydrated to the corresponding cyclic ethers (7c-f, 8h,i,l,n) or lactones (9a,c,f,k) respectively.Finally, alcohols 6b,d,e give, after acid treatment, the Friedel-Crafts type benzocyclopentenes 10b,d,e.
Polyphenylene as an electron transfer catalyst in lithiation processes
Yus, Miguel,Gómez, Cecilia,Candela, Pablo
, p. 6207 - 6210 (2007/10/03)
The lithiation of different functionalised chlorinated materials (1a-c), dichlorinated compounds (1d-f) and benzofused cyclic ethers (1g,h) with lithium powder in the presence of catalytic amounts of either linear (LPP) or crosslinked (CPP) polyphenylene, in THF at temperatures ranging between -78 and 20°C, leads to the expected organolithium intermediates (Ia-h), which by reaction with electrophiles [ButCHO, PhCHO, Et2CO, (CH2)5CO, PhCOMe, Me3SiCl] gives, after hydrolysis with water, the expected products 2aa-hf.