LITHIATED BENZYLLITHIUMS FROM CHLOROBENZYL CHLORIDES BY A DTBB-CATALYZED LITHIATION

Authors
GOMEZ C HUERTA FF YUS M
Citation
C. Gomez et al., LITHIATED BENZYLLITHIUMS FROM CHLOROBENZYL CHLORIDES BY A DTBB-CATALYZED LITHIATION, Tetrahedron letters, 38(4), 1997, pp. 687-690
Citations number
13
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
4
Year of publication
1997
Pages
687 - 690
Database
ISI
SICI code
0040-4039(1997)38:4<687:LBFCCB>2.0.ZU;2-O
Abstract
The reaction of 2-, 3- or 4-chlorobenzyl chlorides (1a-c) with an exce ss of lithium and a catalytic amount of DTBB (7 mol%) in the presence of different electrophiles [(PrCHO)-C-i, Bu(t)CHO, Et(2)CO(1) (CH2)(5) CO, PhCOMe, Me(3)SiCl] in THF at -50 degrees C leads after hydrolysis with water, to the expected dioles or disilylated compounds 2aa-2cf. ( C) 1997, Elsevier Science Ltd.