METALATION OF ARYLMETHYL METHYL ETHERS AND CONNECTION WITH THEIR REDUCTIVE ELECTROPHILIC SUBSTITUTION

Authors
AZZENA U DEMARTIS S FIORI MG MELLONI G PISANO L
Citation
U. Azzena et al., METALATION OF ARYLMETHYL METHYL ETHERS AND CONNECTION WITH THEIR REDUCTIVE ELECTROPHILIC SUBSTITUTION, Tetrahedron letters, 36(31), 1995, pp. 5641-5644
Citations number
9
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
36
Issue
31
Year of publication
1995
Pages
5641 - 5644
Database
ISI
SICI code
0040-4039(1995)36:31<5641:MOAMEA>2.0.ZU;2-4
Abstract
Stable alpha-methoxy arylmethyl carbanions can be generated by metalat ion of arylmethyl methyl ethers, 1, with n-BuLi in THF at -40 degrees C, avoiding Wittig rearrangement to the corresponding alkoxides 2. Rea ction of these carbanions with various electrophiles afforded the expe cted products 3 in satisfactory yields. Connection between the metalat ion procedure and the reductive electrophilic substitution of arylmeth yl methyl ethers allowed the transformation of compounds 1 into 2-aryl propanoic acids, 5.