282733-20-4Relevant academic research and scientific papers
The application of intramolecular radical cyclizations of acylsilanes in the regiospecific formation of cyclic silyl enol ethers
Huang,Chang,Wang,Tsai
, p. 8983 - 8991 (2001)
Acylsilanes with terminal α-stannyl bromide or xanthate functionalities are prepared, α-Stannyl radicals generated from these acylsilanes undergo intramolecular cyclizations to give cyclic silyl enol ethers regiospecifically. The radical processes involve radical cyclization, Brook rearrangement, and β-fragmentation in sequence. A tributylstannyl group serves as the radical leaving group. The newly formed σ-bond and π-bond are located between the same two carbon atoms. This approach is limited to the formation of five-membered rings. In another route, ω-bromo-α-phenylsulfonylacylsilanes are synthesized. The radical cyclizations of these α-sulfonylacylsilanes also give cyclic silyl enol ethers. The phenylsulfonyl moiety is the radical leaving group in this system. Furthermore, the newly formed σ-bond and π-bond are located at adjacent positions sharing a single carbon atom. The latter approach is effective for both five- and six-membered ring formation.
α-Sulfenylation of acylsilanes and aldehydes with N- (phenylthio)succinimide
Huang, Chih-Hao,Liao, Kang-Shyang,De, Surya Kanta,Tsai, Yeun-Min
, p. 3911 - 3914 (2007/10/03)
The reactions of acylsilanes with N-(phenylthio)succinimide in the presence of p-toluenesulfonic acid in acetonitrile give α-sulfenylated acylsilanes in good yields. Aldehydes with α-alkyl substituent afford moderate yields of α-sulfenylated products unde
