78522-84-6Relevant articles and documents
Highly chemoselective lithium metal reductions of benzaldehyde bis(2-methoxyethyl) acetals
Von Schrader, Thomas,Woodward, Simon
, p. 3833 - 3836 (2007/10/03)
Naphthalene-catalysed reductions of PhCH(OR)2 (R = Me, CH2CH2OMe) acetals by lithium metal, followed by reactions with electrophiles (H+, TMSCl, nBuBr, CH2=CHCH2Br), proceed with high chemoselectivity when the reductions are carried out at -90 °C especially for R = CH2CH2OMe. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany 2002.
Metalation of arylmethyl alkyl ethers
Azzena, Ugo,Pilo, Luciano,Sechi, Alessandra
, p. 12389 - 12398 (2007/10/03)
Arylmethyl alkyl ethers 1a-11 were metallated with n-BuLi or sec-BuLi in THF at different temperatures, affording α-alkoxy-substituted arylmethyllithium derivatives. At low temperature, the organometallics derived from methyl and isopropyl ethers are suff
Metalation of Arylmethyl Methyl Ethers and Connection with Their Reductive Electrophilic Substitution
Azzena, Ugo,Demartis, Salvatore,Fiori, Maria Giovanna,Melloni, Giovanni,Pisano, Luisa
, p. 5641 - 5644 (2007/10/02)
Stable α-methoxy arylmethyl carbanions can be generated by metalation of arylmethyl methyl ethers, 1, with n-BuLi in THF at -40 degC, avoiding Wittig rearrengement to the corresponding alkoxides 2.Reaction of these carbanions with various electrophiles afforded the expected products 3 in satisfactory yields.Connection between the metalation procedure and the reductive electrophilic substitution of arylmethyl methyl ethers allowed the transformation of compounds 1 into 2-arylpropanoic acids, 5.
