Citation
G. Maas et S. Bender, Novel alpha-silyl-alpha-diazoacetates containing a silicon-heteroatom bond, SYNTHESIS-S, (7), 1999, pp. 1175-1180
Citations number
29
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
SYNTHESIS-STUTTGART
ISSN journal
00397881
→ ACNP
Issue
7
Year of publication
1999
Pages
1175 - 1180
Database
ISI
SICI code
0039-7881(199907):7<1175:NACASB>2.0.ZU;2-0
Abstract
Silylation of diazoacetic esters with (t-Bu)(2)Si(Cl)OTf or Ph(t-Bu)Si(Cl)O
Tf (Tf = SO2CF3) yields alpha(chrorosilyl)-alpha-diazoacetates 3a-d, which
can be converted into azidosilyl- (7), isocyanatosilyl- (8), and isothiocya
natosilyl- (9) substituted diazoacetates. Acid-catalyzed hydrolysis of 8a o
r 9a generates (hydroxysilyl)diazoacetate 10. (Allylaminosilyl)diazoacetate
s 12a,b can be prepared from diisopropylsilyl bis(triflate) by successive t
reatment with diazoacetic esters and allylamine.