136116-42-2Relevant academic research and scientific papers
tert-Butyldimethylsilyldihalomethyllithium as a dihalomethylene dianion synthon. 1,3-Rearrangement and 1,4-rearrangement of silyl group from carbon to oxide
Shinokubo, Hiroshi,Miura, Katsukiyo,Oshima, Koichiro,Utimoto, Kiitiro
, p. 503 - 514 (1996)
One-pot synthesis of R1CH(OSiMe2-t-Bu)CX2CH(OH)R2 (X = Cl, Br) by successive addition of two different aldehydes (R1CHO and R2CHO) has been achieved starting from tert-butyldimethylsilyldihalomethyllithium. Treatment of a THF solution of the title carbanion (X = Cl) with p-MeOC6H4CHO or n-BuCHO followed by an addition of HMPA and benzaldehyde gave the corresponding 1,3-diol monosilyl ether in 83% or 45% yield, respectively. The use of oxirane in place of aldehyde as the first electrophile followed by addition of benzaldehyde provided 1,4-diol monosilyl ether.
Effective silylation of carboxylic acids under solvent-free conditions with tert-butyldimethylsilyl chloride (TBDMSCL) and triisopropylsilyl chloride (TIPSCL)
Firouzabadi, Habib,Iranpoor, Naser,Shaterian, Hamid Reza
, p. 71 - 81 (2007/10/03)
Varions types of carboxylic acids can be converted effectively to their corresponding TBDMS and TIPS esters using TBDMSCI and TIPSCI in the presence of imidazole under solvent-free conditions. The advantage of this modified method in comparison with that reported by Corey is the elimination of DMF, which eliminates aqueous work-up. The method is not a time-consuming process and the reactions proceed spontaneously. By this method, absolute chemoselectivity for the protection of carboxylic acid functions in the presence of 2°, 3° hydroxyl groups are observed.
Efficient and chemoselective protection of alcohols and phenols with tert-butyldimethylchlorosilane (TBDMCS) under solvent-free conditions
Firouzabadi, Habib,Etemadi, Shahrad,Karimi, Babak,Jarrahpour, Ali Asghar
, p. 45 - 51 (2007/10/03)
Various types of primary and secondary alcohols and phenols can be converted efficiently to their corresponding TBDMS ethers using TBDMCS/imidazole under solvent-free conditions. Elimination of DMF, accompanied with an easy non-aqueous work-up and a high rate enhancement of the reaction are worthy to be mentioned for the presented method. The reactions show absolute chemoselectivity for the protection of primary in the presence of secondary alcohols.
tert-Butyldimethylsilyldichloromethyllithium as a dichloromethylene dianion synthon. 1,3-Rearrangement of silyl group from carbon to oxide
Shinokubo, Hiroshi,Miura, Katsukiyo,Oshima, Koichiro,Utimoto, Kiitiro
, p. 1951 - 1954 (2007/10/02)
One-pot synthesis of R1CH(OSiMe2-t-Bu)CCl2CH(OH)R2 by successive addition of two different electrophiles has been achieved starting.
