Tetrahedron

tert-Butyldimethylsilyldihalomethyllithium as a dihalomethylene dianion synthon. 1, 3-Rearrangement and 1, 4-rearrangement of silyl group from carbon to oxide

H Shinokubo, K Miura, K Oshima, K Utimoto

Index: Shinokubo, Hiroshi; Miura, Katsukiyo; Oshima, Koichiro; Utimoto, Kiitiro Tetrahedron, 1996 , vol. 52, # 2 p. 503 - 514

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Citation Number: 60

Abstract

One-pot synthesis of R1CH (OSiMe2-t-Bu) CX2CH (OH) R2 (X= Cl, Br) 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 ...

tert-Butyldimethylsilyldichloromethyllithium as a dichloromethylene dianion synthon. 1, 3-rearrangement of silyl group from carbon to oxide

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Efficient and chemoselective protection of alcohols and phenols with tert-butyldimethylchlorosilane (TBDMCS) under solvent-free conditions

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Effective silylation of carboxylic acids under solvent-free conditions with tert-butyldimethylsilyl chloride (TBDMSCL) and triisopropylsilyl chloride (TIPSCL)

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