155397-12-9Relevant articles and documents
Cu-Catalyzed Carbonylative Silylation of Alkyl Halides: Efficient Access to Acylsilanes
Cheng, Li-Jie,Mankad, Neal P.
supporting information, p. 80 - 84 (2020/01/09)
A Cu-catalyzed carbonylative silylation of unactivated alkyl halides has been developed, enabling efficient synthesis of alkyl-substituted acylsilanes in high yield. A variety of functional groups are tolerated under the mild reaction conditions, and prim
Can relief of ring-strain in a cyclopropylmethyllithium drive the Brook rearrangement?
Clayden, Jonathan,Watson, David W.,Chambers, Mark
, p. 3195 - 3203 (2007/10/03)
α-Cyclopropyl-α-trialkylsilyl alkoxides were formed either by addition of cyclopropyllithiums to acylsilanes or by addition of organolithiums to a cyclopropylformylsilane. [1,2]-Brook rearrangement led to α-silyloxy organolithiums which on warming underwent cyclopropane ring opening and [1,5]-retro-Brook rearrangement to yield γ-silyl ketones. Despite the favourability of the cyclopropane ring opening, the Brook rearrangement still required the presence of an anion stabilising group to proceed. β-Silylketones were similarly formed by Brook-retro-Brook rearrangement on warming acylsilanes with a vinyllithium.
The reactions of phenyldimethylsilyllithium with nitriles
Fleming, Ian,Solay, Monica,Stolwijk, Frederik
, p. 121 - 124 (2007/10/03)
Phenyldimethylsilyllithium reacts with nitriles by several substantially different pathways depending upon the structure of the nitrile. The products include the acylsilane 2 from pivalonitrile (1), cumylsilane 5 from 2-phenylisobutyronitrile (4), the α-anion from phenylacetonitrile (9), and a mixture of benzil (15) and 2,4,5-triphenylimidazole (17) from benzonitrile (13).