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Reaction of Et 3SiH+KO tBu with diaryl ethers, sulfides and amines that feature an ortho alkyl group leads to rearrangement products. The rearrangements arise from formation of benzyl radicals, likely formed through hydrogen atom abstraction by triethylsilyl radicals. The rearrangements involve cyclisation of the benzyl radical onto the partner arene, which, from computation, is the rate determining step. In the case of diaryl ethers, Truce-Smiles rearrangements arise from radical cyclisations to form 5-membered rings, but for diarylamines, cyclisations to form dihydroacridines are observed. (Figure presented.).
|Number of pages||8|
|Journal||Advanced Synthesis and Catalysis|
|Early online date||14 Apr 2020|
|Publication status||Published - 26 May 2020|
- Truce-Smiles rearrangement
FingerprintDive into the research topics of 'Benzylic C-H functionalisation by [Et3SiH + KOtBu] leads to radical rearrangements in o-tolylaryl ethers, amines'. Together they form a unique fingerprint.
- 1 Finished
E Infrastructure Bid - Capital Equipment Bid
Littlejohn, D., Fedorov, M., Mulheran, P. & Reese, J.
EPSRC (Engineering and Physical Sciences Research Council)
20/01/12 → 31/03/12