18036-83-4Relevant academic research and scientific papers
2-(Trimethylsilyl)phenyl Trimethylsilyl Ethers as Stable and Readily Accessible Benzyne Precursors
Ikawa, Takashi,Masuda, Shigeaki,Nakajima, Hiroki,Akai, Shuji
, p. 4242 - 4253 (2017/04/27)
Stable 2-(trimethylsilyl)phenyl trimethylsilyl ethers, readily obtained from the corresponding halogenated phenols in two steps, were identified as novel benzyne precursors. These species were converted to benzynes by a domino reaction of O-desilylation,
Improved synthesis of the benzyne precursor 2-(trimethylsilyl)phenyl trifluoromethanesulfonate
Atkinson, Darcy J.,Sperry, Jonathan,Brimble, Margaret A.
experimental part, p. 911 - 913 (2010/04/29)
An alternate procedure for the preparation of 2-(trimethylsilyl)phenyl trifluoromethanesulfonate, a coveted benzyne precursor, is described. Modifications to existing methods result in a dramatic reduction in the overall reaction time and eliminate the us
Interaction of alkoxides. XVIII. Utilitization of the complex base from alkyllithium and potassium alkoxides in the dimetallation of phenol, thiophenol, o-, m- and p-cresol
Andringa, H.,Verkruijsse, H.D.,Brandsma, L.,Lochmann, L.
, p. 307 - 314 (2007/10/02)
Successful O- and ortho-ring metallation of phenol and side chain metallation in o-cresol has been achieved by use of a mixture of two molar equivalents of n-butyllithium, one molar equivalent of potassium t-butoxide and two molar equivalents of N,N,N',N'-tetramethylethylene diamine in hexane.Poor results were obtained with m-cresol, thiophenol and p-cresol. m-Cresol was effectively dimetallated with a mixture of two molar equivalents of tBuOK and two molar equivalents of nBuLi*TMEDA.The effectiveness of another type of complex base based on 2-ethylhexyllithium (EhexLi) and potassium alkoxides has been also investigated, especially in respect of the influence of the concentration and the ctructure of the alkoxide used.With a complex base from EhexLi and 3 equivalents of potassium 3-methyl-3-pentoxide phenol was successfuly dimetallated even in the absence of TMEDA.Thus, the enhanced reactivity of a complex base containing a higher concentration of a more branched potassium alkoxide over that of previously used complex bases has been confirmed.
Reactions of o-Lithio-lithiumphenolate and o-Lithio-N-methyl-lithiumanilide with Halides of Phosphorus, Arsenic and Silicon
Heinicke, J.,Tzschach, A.
, p. 232 - 237 (2007/10/02)
The title compounds and chlorides of the type ClERn (E=P, As, Si) react smoothly in a molecular ratio of 1:2 to give the corresponding disubstituted phenole and N-methylaniline derivatives, respectively.Attempts with an 1:1 ratio show different results de
