The trimethylsilyl-group can tolerate the nitrating mixture such as HNO3+AcOH. The similar compound can be easily nitrated but I am worrying about TMS present on it.
Kumar,
You are right the trimethylsilyl group may be replaced by NO2 as reported
--- Sun, Qun, Faming Zhuanli Shenqing, 102898452, 30 Jan 2013
--- Aitken, K. M. and Aitken, R. A. Science of Synthesis, 31b, 1183-1320; 2007
--- Lothian, Aileen P. et al Tetrahedron, 67(15), 2788-2793; 2011
However, I would like you to look at
--- Damja, Ramadan I. et al Journal of Organometallic Chemistry, 291(1), 25-33; 1985
--- Yamakawa, Takeru et al Journal of Medicinal Chemistry, 33(5), 1430-7; 1990
where they were able to isolate some nitrated silyl product(s).
Good luck
It depends on what the TMS group is attached to.
O-TMS = No, not stable to acid
Aromatic TMS groups will generally undergo ipso electrophilic aromatic substitution faster than a proton. The wheland intermediate is additionally stabilised by the beta-silicon effect.
A vinyl or alkynyl or allyl TMS group might be stable but also react with electrophiles to generate the corresponding beta carbocation that generally results in a loss of TMS. However the required conditions are a bit more forcing.
An alkyl or benzyl TMS will be stable.
I don't think this answers your question exactly, but try using Bi(NO3)3 as a nitrating agent. It is a documented procedure that works with fairly sensitive aromatics.
The TMS group is generally somewhat acid-labile. You may consider TIPS or TBDPS groups, which are normally more stable in acid. However, their removal also tends to require harsher conditions. Good luck!
I speculate the reverse way can be performed easily i.e. 1st nitration followed by -TMS insertion using LDA or some other. But if I get it whether the -NO2 group can be reduced easily by using neutral condition like SnCl2 in ethanol. Although I am still worrying about -TMS group.
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