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Chloracylierung und Bromacylierung von Carbonylverbindungen. IV. Bildungsmechanismus von Carbonsäure‐(1‐halogenalkyl)estern
Author(s) -
Bigler Peter,
Neuenschwander Markus
Publication year - 1978
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19780610711
Subject(s) - chemistry , benzoyl chloride , aldehyde , chloride , medicinal chemistry , acetyl chloride , acyl chloride , lewis acids and bases , order of reaction , reaction mechanism , reaction rate , catalysis , organic chemistry , polymer chemistry , kinetics , reaction rate constant , physics , quantum mechanics
Chloroacylation and bromoacylation of carbonyl compounds IV. Investigations of the reaction mechanism The kinetics of the Lewis acid catalyzed reaction between acyl chlorides and carbonyl compounds (especially aldehydes) is investigated by 1 H‐NMR.‐spectroscopy. With acetyl chloride as starting material a second order reaction is observed; the rate of the reaction increases in polar solvents as well as with increasing electron‐donating capacity of the aldehyde. ‐ With benzoyl chloride as starting material the reaction is first order with respect to benzoyl chloride, but zero order with respect to the aldehyde. The reaction rate is strongly influenced by the substituents of the benzoyl chloride. ‐ Two polar reaction mechanisms which are in accord with these results are outlined and discussed.