SINGLE AND DOUBLE REDUCTIVE CLEAVAGE OF C-O BONDS OF AROMATIC DIMETHYL ACETALS AND KETALS - GENERATION OF BENZYLIC MONOCARBANIONS AND DICARBANIONS

Authors
AZZENA U MELLONI G PISANO L SECHI B
Citation
U. Azzena et al., SINGLE AND DOUBLE REDUCTIVE CLEAVAGE OF C-O BONDS OF AROMATIC DIMETHYL ACETALS AND KETALS - GENERATION OF BENZYLIC MONOCARBANIONS AND DICARBANIONS, Tetrahedron letters, 35(36), 1994, pp. 6759-6762
Citations number
14
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
35
Issue
36
Year of publication
1994
Pages
6759 - 6762
Database
ISI
SICI code
0040-4039(1994)35:36<6759:SADRCO>2.0.ZU;2-U
Abstract
The reductive cleavage of aromatic dimethyl acetals and ketals, 1, wit h Li metal in THF at low temperature allows the generation of stable a lpha-alkoxy-alpha-arylsubstituted carbanions, avoiding the Wittig rear rangement. Reaction of these carbanions with various electrophiles aff orded the expected products 2. Further in situ reaction of compounds 2 afforded the products of reductive electrophilic disubstitution, 3.