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First Authentication of Kostanecki 's Triketone and Multimolecular Reaction of Aromatic Aldehydes with Acetophenone
Author(s) -
Shan Zixing,
Hu Xiaoyun,
Hu Lin,
Peng Xitian
Publication year - 2009
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.200800413
Subject(s) - chemistry , cyclohexanol , acetophenone , deprotonation , catalysis , pentane , single crystal , medicinal chemistry , organic chemistry , stereochemistry , crystallography , ion
AbstractA double‐component, multimolecular reaction between acetophenone and aromatic aldehydes was achieved under catalysis by the solid‐base mixture NaOH/K 2 CO 3 , and Kostanecki 's triketone, supposed to exist for more than 110 years, was successfully separated for the first time as an accompaniment of a pentane‐1,5‐dione or a 1,2,3,4,5‐pentasubstituted cyclohexanol ( Scheme 1 ) and authenticated by spectroscopic and single‐crystal X‐ray diffraction analysis. Thus, the multimolecular‐reaction mechanism of the formation of 1,2,3,4,5‐pentasubstituted cyclohexanols from 1‐phenylalkan‐1‐ones and aromatic aldehydes was fully validated based on the results ( Scheme 3 ).