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Controlled Stepwise Release of Fragrance Alcohols from Dendrimer‐Based 2‐Carbamoylbenzoates by Neighbouring Group Participation
Author(s) -
Frérot Eric,
Herbal Karim,
Herrmann Andreas
Publication year - 2003
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200390152
Subject(s) - chemistry , dendrimer , steric effects , intramolecular force , hydrolysis , reaction rate constant , kinetic resolution , organic chemistry , polymer chemistry , medicinal chemistry , kinetics , catalysis , enantioselective synthesis , physics , quantum mechanics
2‐Carbamoylbenzoates which are chemically bound to the surface of dendrimers were found to release tertiary fragrance alcohols by neighbouring group assisted alkaline hydrolysis under mild reaction conditions. Owing to the excellent separation of the intermediate reaction products by analytical HPLC, the kinetic rate constants of the first two consecutive reaction steps of fragrance release could be determined for a series of modified dendrimers with increasing size. Because of the intramolecular neighbouring group effect, the kinetic rate constants were found to be independent of the dendrimer generation and are not influenced by steric effects on the surface of the macromolecules. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)