105200-30-4Relevant academic research and scientific papers
Preparation and Some Reactions of Compounds of the Type (Me3Si)2C(SiMe2OMe)(SiMe2X). Anchimeric Assistance by the Methoxy Group
Al-Wassil, Abdulaziz I.,Eaborn, Colin,Romanelli, M. Novella
, p. 1363 - 1366 (2007/10/02)
Because of anchimeric assistance by the γ-OMe group the compound R2C(SiMe2OMe)(SiMe2Cl) (1) (R = SiMe3 throughout), in contrast to the closely related R3CSiMe2Cl, reacts readily with silver salts; thus reactions with AgY or AgBF4 give the compounds R2C(SiMe2OMe)(SiMe2X) with X= ONO2, NCO, OCOCF3, OCOMe, OCOPh, OSO2C6H4Me-p, or F.The anchimeric assistance is so great that even the hydride R2C(SiMe2OMe)(SiMe2H) reacts with silver salts; thus AgOCOCF3 gives R2C(SiMe2OMe)(SiMe2OCOCF3).The azide R2C(SiMe2OMe)(SiMe2N3) was made by treatment of (1) with NaN3 in (MeOCH2)2.Treatment of (1) with water in dioxane gives R2C(SiMe2OMe)(SiMe2OH) in the presence of Et3N and R2C(SiMe2OH)2 in its absence.Likewise reaction with CF3CH2OH gives R2C(SiMe2OMe)(SiMeOCH2CF3) in the presence of EtN3 and R2C(SiMe2OCH2CF3)2 in its absence.The bis(trifluoroacetate) R2C(SiMe2OCOCF3)2 reacts with MeOH more slowly than R2C(SiMe2OMe)(SiMe2OCOCF3), indicating that the γ-OCOCF3 provides less anchimeric assistance than the γ-OMe group.
