RETRO CLAISEN CLEAVAGE OF ALPHA-NITROCYCLOALKANONES USING TRIMETHYLSILYLMETHYLMAGNESIUM CHLORIDE (PETERSON REAGENT) - SYNTHESIS OF FUNCTIONALIZED BETA-KETO-TRIMETHYLSILANES

Authors
BALLINI R BARTOLI G GIOVANNINI R MARCANTONI E PETRINI M
Citation
R. Ballini et al., RETRO CLAISEN CLEAVAGE OF ALPHA-NITROCYCLOALKANONES USING TRIMETHYLSILYLMETHYLMAGNESIUM CHLORIDE (PETERSON REAGENT) - SYNTHESIS OF FUNCTIONALIZED BETA-KETO-TRIMETHYLSILANES, Tetrahedron letters, 34(20), 1993, pp. 3301-3304
Citations number
15
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
34
Issue
20
Year of publication
1993
Pages
3301 - 3304
Database
ISI
SICI code
0040-4039(1993)34:20<3301:RCCOAU>2.0.ZU;2-4
Abstract
Beta-ketosilanes, bearing a nitro functionality, can be prepared by nu cleophilic ring cleavage of alpha-nitrocycloalkanones with the Peterso n reagent. This high yielding process shows considerable chemoselectiv ity but fails with large rings (C(n)>7). This unusual reactivity is te ntatively explained considering the silicon beta effect.