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Deprotonation of 1‐(carbethoxyalkyl)pyridinium halides with strong N‐bases
Author(s) -
DegaSzafran Zofia,
Schroeder Grzegorz,
Szafran Mirosław
Publication year - 1999
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/(sici)1099-1395(199901)12:1<39::aid-poc84>3.0.co;2-4
Subject(s) - chemistry , pyridinium , deprotonation , bromide , halide , pyridine , medicinal chemistry , chloride , ylide , acetonitrile , photochemistry , inorganic chemistry , organic chemistry , ion
The rate constants were measured for deprotonation of 1‐(carbethoxymethyl)pyridinium chloride and 1‐(2‐carbethoxyethyl)pyridinium bromide with strong bases (DBU, MTBD, TBD and P2‐Et) in acetonitrile. The UV spectra and semiempirical calculations are consistent with an ylide structure of the deprotonated species. The ylides obtained slowly decompose, and the reaction products were identified by 1 H NMR spectroscopy; 1‐(carbethoxymethyl)pyridinium chloride gives N ‐methylpyridinium cation and ethanol and 1‐(2‐carbethoxyethyl)pyridinium bromide converts to pyridine and ethyl acrylate. Copyright © 1999 John Wiley & Sons, Ltd.