128588-77-2Relevant academic research and scientific papers
PREPARATION AND RING-OPENING REACTIONS OF 2-PHENYLSULPHONYL-2-TRIMETHYLSILYL OXIRANES
Hewkin, Cheryl T.,Jackson, Richard F. W.
, p. 1877 - 1880 (1990)
Reaction of 2-phenylsulphonyl oxiranes (1) with butyllithium in the presence of chlorotrimethylsilane gave 2-phenylsulphonyl-2-trimethylsilyl oxiranes (2), which on treatment with MgBr2*Et2O gave 2-bromoacylsilanes (3) and either bromovinyl sulphones (5)
A New Method for the Synthesis of α-Bromoacyl Silanes via Ring-opening of 2-Phenylsulphonyl-2-trimethylsilyloxiranes
Hewkin, Cheryl T.,Jackson, Richard F. W.
, p. 3103 - 3112 (2007/10/02)
2-Phenylsulphonyl-2-trimethylsilyloxiranes 2 are efficiently prepared by treatment of 2-phenyl-sulphonyloxiranes 3 with butyllithium in the presence of chlorotrimethylsilane at low temperatures.Reaction of 3-alkyl-2-phenylsulphonyl-2-trimethylsilyloxiranes 2, in which the alkyl group is primary, with magnesium bromide at room temperature gives 2-bromoacyl silanes 1 in good yield.Reaction at higher temperatures leads to competing formation of bromovinyl sulphones 7.Reaction of 3,3-dialkyloxiranes with magnesium bromide occurs much more readily, leading to 2-bromoacyl silanes 1 in moderate yields.Other products derived from a common carbocationic intermediate are also isolated.
