Journal
TETRAHEDRON
Volume 61, Issue 13, Pages 3245-3249Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2004.10.098
Keywords
metallation; pyridines; in situ IR; mechanism; deuteration
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Deprotonation of 3,5-dichloropyridine using LTMP and BuLi was monitored in real time by infrared spectroscopy. It appeared that the substrate was rapidly deprotonated. Transient structures between the substrate and the lithio derivative were detected. The absorbances recorded for the lithio derivative showed that the structures obtained using LTMP and BuLi were similar. When BuLi was used to deprotonate, a complete deuteration of the lithio derivative was noted upon quenching with D2O. The latter did not allow the quantification of the lithio derivative when LTMP was used, since only partial deuteration was observed. (c) 2004 Elsevier Ltd. All rights reserved.
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