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Nachbarǵruppeneffekte bei der Hydrolyse von Acetonyl‐Estern
Author(s) -
Schätzle Elsbeth,
Urheim Hans,
Thürkauf Max,
Rottenberg Max
Publication year - 1963
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.19630460659
Subject(s) - chemistry , electrophile , nucleophile , hydrolysis , catalysis , stereochemistry , medicinal chemistry , organic chemistry
Kinetic studies revealed that esters of hydroxyacetone undergo alkaline hydrolysis with participation of neighbouring groups, its rate being higher by a factor of at least 20 than could have been anticipated on the basis of inductive effects alone. The mechanism is discussed in terms of either nucleophilic or electrophilic intra‐molecular catalysis.