75031-68-4Relevant academic research and scientific papers
The Scope and Limitations of Intramolecular Radical Cyclizations of Acylsilanes with Alkyl, Aryl, and Vinyl Radicals
Chang, Sheng-Yueh,Jiaang, Weir-Torn,Cherng, Chaur-Donp,Tang, Kuo-Hsiang,Huang, Chih-Hao,Tsai, Yeun-Min
, p. 9089 - 9098 (2007/10/03)
5-Exo cyclizations of primary and secondary radicals with acylsilanes successfully give cyclopentyl silyl ethers. The corresponding 6-exo cyclizations are sensitive to changes of the size of silyl groups. Secondary radicals undergo 6-exo cyclizations with
Nonionic superbase-catalyzed silylation of alcohols
D'Sa, Bosco A.,McLeod, Dale,Verkade, John G.
, p. 5057 - 5061 (2007/10/03)
Herein we report a very effective and mild procedure for the silyl protection of a wide variety of substrate alcohols, including primary, secondary, allylic, propargylic, benzylic, hindered secondary, tertiary, acid-sensitive, and base-sensitive alcohols and also hindered phenols. The silylation reagent used is tert-butyldimethylsilyl chloride (TBDMSCl) and the catalyst is P(MeNCH2CH2)3N, 1b, both of which are commercially available. The reactions are carried out in acetonitrile from 24 to 40 °C and on rare occasions in DMF from 24 to 80 °C. The effect of solvent, catalyst concentration, and temperature and reaction time on the silylation of alcohols and the excellent compatibility of our method with a variety of functional groups is discussed. An efficient method for recycling the catalyst is also presented. Although representative primary alcohols, secondary alcohols, and phenols were silylated using the more sterically hindered reagent tert-butyldiphenylsilyl chloride (TBDPSCl) in the presence of lb as a catalyst, tertiary alcohols were recovered unchanged.
A mild method for rapid tert-Butyldiphenylsilylation of primary and secondary alcohols
Hardinger, Steven A.,Wijaya, Ngadi
, p. 3821 - 3824 (2007/10/02)
A rapid and efficient method for the protection of primary and secondary alcohols as their tert-butyldiphenylsilyl (tBDPS) ethers was developed. Reaction of the alcohol and tBDPSCl in DMF with AgNO3, NH4NO3, or NH4ClO4 provides good yields of the corresponding silyl ethers.
