29539-18-2Relevant articles and documents
Cyclic acetals as precursors of substituted isochromans and naphthoxepines
Garcia, Daniel,Foubelo, Francisco,Yus, Miguel
, p. 507 - 519 (2008/09/18)
The reaction of 6,8-dioxabenzocycloheptenes 3 or 8,10-dioxacycloocta[de]naphthalenes 5 [easily prepared from the dibenzylic diols 1 and 4, respectively, and a carbonyl compound] with an excess of lithium and a catalytic amount of DTBB (2.5 mol %) in THF a
Improved procedure for 3,4-dihydro-1H-2-benzopyran ring closure. A general access to 3-substituted isochromanes
Antonioletti, Roberto,Bovicelli, Paolo,Crescenzi, Benedetta,Lupattelli, Paolo
, p. 6751 - 6752 (2007/10/03)
A general method for the ring closure of 1-substituted 2-(- hydroxymethyl)-phenylethanols to 3-substituted isochromanes using p-TsOH supported on silica gel is reported.
1,2-Di(lithiomethyl)benzene from Phthalan: Sequential Introduction of Two Different Electrophiles
Almena, Juan,Foubelo, Francisco,Yus, Miguel
, p. 3351 - 3364 (2007/10/02)
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.