Novel DMAP-catalyzed skeletal rearrangement of 5-exo-(2-hydroxy-ethylene)oxasilacyclopentanes.
[reaction: see text] 5-exo-(Hydroxyethylene)-2-oxa-1-silacyclopentanes are found to undergo a novel DMAP-catalyzed skeletal rearrangement through silicon-oxygen exchange during acetylation to yield the corresponding 5-(2-acetoxyalkyl)-2-oxa-1-silacyclopent-4-enes exclusively. The mechanism for this unprecedented rearrangement is proposed.
Bonafoux
D
D
Department of Chemistry, State University of New York at Stony Brook, 11794-3400, USA.
Ojima
I
I
D018360:Crystallography, X-Ray; D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000737:chemistry*; D011725:Pyridines / Q000737:chemistry*; D012821:Silanes / Q000138:chemical synthesis*
C417980:4-(dimethylamine)pyridine; D003517:Cyclopentanes; D011725:Pyridines; D012821:Silanes