A new route to silyl-substituted cyclobutenones and silylketenes

A new route to silyl-substituted cyclobutenones and silylketenes

2-Silyl-cyclobutenones are obtained by an addition/substitution approach on dimethyl squarate using silyl anions and undergo electrocyclic ring opening to reactive silyl(vinyl)ketenes. 2-Silyl-cyclobutene(di)ones are obtained by an addition/substitution approach on dimethyl squarate using silyl anio...

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Veröffentlicht in:Tetrahedron letters 2011-01, Vol.52 (1), p.46-48
Hauptverfasser: Benda, Konstantin, Knoth, Tanja, Danheiser, Rick L., Schaumann, Ernst
Format: Artikel
Sprache:eng
Schlagworte:
anions
chemical reactions
Cycloaddition reactions
Cyclobutenones
Cyclopentenones
organic compounds
Silyl anions
Silylketenes
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Zusammenfassung:2-Silyl-cyclobutenones are obtained by an addition/substitution approach on dimethyl squarate using silyl anions and undergo electrocyclic ring opening to reactive silyl(vinyl)ketenes. 2-Silyl-cyclobutene(di)ones are obtained by an addition/substitution approach on dimethyl squarate using silyl anions. The acetal and in particular the thioacetal derivatives readily undergo electrocyclic ring opening to reactive silyl(vinyl)ketenes.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2010.10.130