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• W1993397029 abstract "Solutions of 2-lithio-5-methylthiophene (4) were characterized using DNMR techniques and shown to be a mixture of monomer and dimer in THF–Et 2 O (3:2). The hypervalent iodine ate complex 5 (Ar 2 I – Li + ), a presumed intermediate in the Li–I exchange with 2-iodo-5-methylthiophene, was observed by 13 C and 7 Li NMR spectroscopy at low temperatures (–130 °C). At higher temperatures, the ate complex coalesced with 2-lithio-5-methylthiophene. A kinetic scheme was developed, which accounts for the exchange of the monomer 4M, dimer 4D, and 2-iodo-5-methylthiophene (6) with the ate complex 5. The rates of the various exchanges were obtained through a DNMR analysis of the variable temperature 13 C and 7 Li NMR spectra, and the thermodynamic and activation parameters were calculated. The monomer 4M and the ate complex 5 have similar reactivity as aryl donors in the Li–I exchange reaction, but 4M is at least 1000 times as reactive as the dimer 4D towards the iodide.Key words: halogen–metal exchange, lithium iodinate, iodine ate complex, lithium reagent, aggregate reactivity." @default.
• W1993397029 created "2016-06-24" @default.
• W1993397029 creator A5060591151 @default.
• W1993397029 creator A5083802387 @default.
• W1993397029 date "2005-09-01" @default.
• W1993397029 modified "2023-10-01" @default.
• W1993397029 title "Mechanism of the lithium–iodine exchange in an iodothiophene" @default.
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• W1993397029 doi "https://doi.org/10.1139/v05-173" @default.
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