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Reduction of Thiocarbonyl Compounds with Lithium Diisopropylamide
Author(s) -
Gebert Andreas,
Jasiński Marcin,
Mlostoń Grzegorz,
Heimgartner Heinz
Publication year - 2014
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.201400130
Subject(s) - lithium diisopropylamide , chemistry , lithium (medication) , medicinal chemistry , thiazole , stereochemistry , organic chemistry , ion , medicine , deprotonation , endocrinology
Treatment of 4,4‐disubstituted 2‐phenyl‐1,3‐thiazole‐5(4 H )‐thiones with lithium diisopropylamide (LDA; LiN i Pr 2 ) in THF at −78° yielded the corresponding 1,3‐thiazole‐5(4 H )‐thioles in moderate yields. Sequential treatment with LDA and MeI under the same conditions led to the 5‐methylsulfanyl derivatives. Similarly, reaction of some cycloalkanethiones as well as diaryl thioketones with LDA and MeI gave cycloalkyl methyl sulfides and diarylmethyl methyl sulfides, respectively. A reaction mechanism via H transfer from LDA to the thiocarbonyl C‐atom via a six‐membered transition state is proposed for this unprecedented reduction of the CS bond.