138566-97-9Relevant academic research and scientific papers
A novel and efficient method for the silylation of alcohols with methallylsilanes catalyzed by Sc(OTf)3
Suzuki,Watahiki,Oriyama
, p. 8903 - 8906 (2000)
Reaction of alcohols with methallylsilanes in the presence of a catalytic amount of Sc(OTf)3 provides efficiently the corresponding alkyl silyl ethers. By using microencapsulated (MC) Sc(OTf)3, which can be easily recovered and reused, yields of alkyl silyl ethers are improved and the work-up process after completion of the reaction is considerably simplified. (C) 2000 Elsevier Science Ltd.
New evidence on the regiochemistry of the tert-butyldiphenylsilylcupration of allene using the silylcuprate or silylcopper reagent
Cuadrado, Purificación,González-Nogal, Ana M.,Sánchez, Alicia,Sarmentero, M. Angeles
, p. 5855 - 5859 (2007/10/03)
The regiochemistry in the tert-butyldiphenylsilylcupration of the allene depends on the temperature and also on the nature of the electrophile. Thus, the intermediate generated by addition of the silylcuprate at -78°C reacted with electrophiles to give allylsilanes, except with oxo compounds which afforded vinylsilanes. On the other hand, the silylcopper reagent was added at -40°C leading, in all cases, to the corresponding allylsilanes. When enones were used as electrophile the vinylsilanes were the 1,2-addition products and the allylsilanes those from 1,4-addition. These functionalized vinyl or allyl tert-butyldiphenylsilanes are interesting synthons for the preparation of conjugated tert-butyldiphenylsilyltrienes and functionalized exocyclic alkylidenecyclopentenes.
The Reaction of tert-Butyldiphenylsilylcuprates with Allenes
Barbero, Asuncion,Cuadrado, Purificacion,Gonzalez, Ana M.,Pulido, Francisco J.,Fleming, Ian
, p. 2811 - 2816 (2007/10/02)
Bis(tert-butyldiphenylsilyl)cuprate 1 reacts with allenes to form allyl- and vinyl-silanes.With allene itself the cuprate reagent shows a different regiochemistry from that of bis(phenyldimethylsilyl)cuprate.The regiochemistry can be controlled by choosing an appropriate reaction temperature.The intermediate cuprate 4 resulting from the addition of 1 to allene reacts with a wide variety of electrophiles giving functionalised allylsilanes.Phenylallenes isomerise to acetylenes.
