Abstract
Benzaldehyde is shown to be a more suitable electrophile than carbon dioxide in reactions involving the lithio derivatives of 2-(N-methylpyrrol-2-yl) oxazolines. The relative reactivities of the C3-Li and C5-Li bonds in ethereal solvents are examined. The 2-oxazolino group at a 2-position in N-substituted pyrrole is shown to possess an activating effect on the 5-position towards lithiation, and eliminates the propensity of the pyrrole nucleus towards polymerisation. The conditions for removal of the 2-protecting group are explored.
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Ngochindo, R.I. 2-Oxazolines as activating groups towards metallation and stabilising groups against polymerization in N-substituted pyrroles. Proc. Indian Acad. Sci. (Chem. Sci.) 104, 377–382 (1992). https://doi.org/10.1007/BF02839547
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DOI: https://doi.org/10.1007/BF02839547