Abstract
The 1,1-bis(methylthio)-5-(4-chlorophenyl)-1,4-pentadien-3-one compound crystallizes in the space group C2/c with unit cell parameters a=25.5763 Å, b=8.08863 Å, c=14.1452 Å, and β=108.6∘. The structure was solved by direct methods and refined to an R-factor of 0.0593. Due to the steric interaction between the two methyl groups, one of the methylthio groups is in cis conformation with C11–C10 double bond and the other is in trans conformation. The cinnamoyl group on the carbonyl carbon atom effects more delocalization of the electrons within the molecule so that the structure is highly conjugated and planar.
Highlights
Cinnamoyl ketene dithioacetals are valuable intermediates in organic synthesis [1,2,3,4]. α-Oxoketene dithioacetals may be considered as highly functionalized α, β-unsaturated ketones which are potential precursors for the regioselective and stereoselective bond formation via 1,2 or 1,4 nucleophilic additions
Conformational studies on diacetyl ketene dithioacetals with bis(methylthio) methylene functionality show a slight twist about the carbon-carbon double bond with the two acyl groups having a highly twisted E,Econformation
The bis(methylthio) group and the phenyl plane are inclined at an angle of only 12.35∘ which is less when compared to the angle between phenyl plane and the dithiolane plane in those structures (32∘ to 35∘)
Summary
Cinnamoyl ketene dithioacetals are valuable intermediates in organic synthesis [1,2,3,4]. α-Oxoketene dithioacetals may be considered as highly functionalized α, β-unsaturated ketones which are potential precursors for the regioselective and stereoselective bond formation via 1,2 or 1,4 nucleophilic additions. Cinnamoyl ketene dithioacetals are valuable intermediates in organic synthesis [1,2,3,4]. Α-Oxoketene dithioacetals may be considered as highly functionalized α, β-unsaturated ketones which are potential precursors for the regioselective and stereoselective bond formation via 1,2 or 1,4 nucleophilic additions. Conformational studies on diacetyl ketene dithioacetals with bis(methylthio) methylene functionality show a slight twist about the carbon-carbon double bond with the two acyl groups having a highly twisted E,Econformation. It is possible that the presence of a cross conjugating group like a styryl group near the carbonyl group could delocalize the electrons more efficiently thereby effecting conformational changes in the title compound
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