Premium
Synthesis and Structures of Fluoroalkylated Triketides
Author(s) -
Büttner Stefan,
Desens Willi,
Michalik Dirk,
Langer Peter
Publication year - 2011
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.201100760
Subject(s) - tautomer , chemistry , enol , keto–enol tautomerism , medicinal chemistry , computational chemistry , organic chemistry , catalysis
The synthesis and structures of fluoroalkylated triketides (3,5‐dioxo esters) and 1,3,5‐triketones – such as 1,1,1‐trifluoroheptane‐2,4,6‐dione – were studied. The synthesis is based on reactions between 1,3‐dicarbonyl dianions and esters. In CDCl 3 , the fluoroalkylated triketides exclusively exist in the forms of enol tautomers. In [D 6 ]DMSO, equilibria between enols and keto hydrates, formed by addition of water to the enols, are observed. In [D 6 ]DMSO, 1,1,1‐trifluoroheptane‐2,4,6‐dione and 5‐chloro‐1,1,1‐trifluoroheptane‐2,4,6‐dione exist exclusively in the forms of their cyclic hemiketals. In CDCl 3 , tautomeric mixtures of the hemiketals and of three open‐chained tautomers are observed (among which the dienol tautomers are predominant).