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Titanocene‐Mediated Homolytic Opening of Epoxysilanes
Author(s) -
Puljic Nicolas,
Albert Matthias,
Dhimane AnneLise,
Fensterbank Louis,
Lacôte Emmanuel,
Malacria Max
Publication year - 2006
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200690213
Subject(s) - chemistry , regioselectivity , homolysis , radical , silylation , adduct , alkyl , medicinal chemistry , ring (chemistry) , chloride , stereochemistry , organic chemistry , catalysis
The titanocene(III) chloride mediated opening of silyloxiranes has been examined. Electron transfer from the metal leads to α ‐silyl radicals with total regiocontrol. The radicals could be trapped by various olefins, and the corresponding adducts were obtained in good yields ( Table ). Further substitution of the oxirane by alkyl groups proved detrimental to the reactions, but ring opening remained essentially regioselective.