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Alkoxycarbonyl‐ and Carboxylate‐Group Migrations in the Benzilic Acid Rearrangement of Ethyl Cyclopropane‐2, 3‐dioxopropionate
Author(s) -
Dahn Hans,
Dao Lê H.,
Hunma Rannoo
Publication year - 1982
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.19820650813
Subject(s) - chemistry , cyclopropane , carboxylate , group (periodic table) , medicinal chemistry , stereochemistry , labelling , rearrangement reaction , organic chemistry , catalysis , ring (chemistry) , biochemistry
In alkaline medium C 3 H 5 COC (OH) 2 COOEt ( 1b ) is transformed into C 3 H 5 C (OH)(COOH) 2 ( 2a ). Labelling experiments show that the cyclopropyl group is not shifted, but only ROOC and/or − O 2 C groups. GC./MS. and NMR. analysis after incomplete reaction show that both ROOC‐ and − O 2 C‐groups Migrate; at higher pH ( ca. 14) the ester group rearrangement seems to be more important than at pH ca. 9‐10.