86123-40-2Relevant academic research and scientific papers
Acylation Reactions of Carbonyl Compounds with 1-Acylpyridinium Salts
Anders, Ernst,Will, Wolfgang,Gassner, Thomas
, p. 1506 - 1519 (2007/10/02)
1-Acyl-4-benzylpyridinium tetrafluoroborates 5 have been used to derive generally applicable guidelines for the reaction of aldehydes 6 and ketones 7 with 1-acylpyridinium salts (scheme 2): a) Non-enolizable aldehydes 6 react with 5 to give N-pyridinium salts 14. b) Enolizable aldehydes 6 can be transformed by means of 5 into pyridinium salts 14 and enol esters 12, respectively.Using aldehyde 6b as an example, it was possible to show that the reaction course (formation of 12 or 14) can be controlled by simple variation of the reaction conditions. c) In general, ketones will not react with 5.The range of applicability of this guidelines has been defined. - We suggest, that the reaction course is mainly determined by the formation of the carbenium ion 19 and the aldehyde-pyridine derivative addition product 8.
