Synthesis of Orthotrithioformates and Related Compounds. Carbanion Formation and Evaluation for 1,4 Addition Reactions with α,β-Unsaturated Ketones

1979 ◽  
Vol 32 (2) ◽  
pp. 353 ◽  
Author(s):  
RAJ Smith ◽  
AR Lal
Keyword(s):  
Addition Reactions ◽  
Unsaturated Ketones ◽  
Related Compounds

The syntheses of potential α-sulfur-substituted carbanion precursors (2a-h) are reported and the results of their subsequent reactions with strong bases are presented. The relatively stable carbanions (3a-d) were made to react with a variety of α,β-unsaturated ketones and the yields of 1,4 and 1,2 addition products were determined.

Highly enantioselective aza-Michael addition reactions of 4-nitrophthalimide with α,β-unsaturated ketones

RSC Advances ◽  
2013 ◽  
Vol 3 (29) ◽  
pp. 11498 ◽  
Author(s):  
Shijun Ma ◽  
Lulu Wu ◽  
Ming Liu ◽  
Xiufang Xu ◽  
Yaodong Huang ◽  
...  
Keyword(s):  
Michael Addition ◽  
Addition Reactions ◽  
Unsaturated Ketones

Conformational analysis of the products of 1,4 addition of Tri(phenylthio)methyllithium to α,β-unsaturated ketones. The X-ray structuredetermination of 4-Phenyl-5,5,5-tri(phenylthio)pentan-2-one

1981 ◽  
Vol 34 (12) ◽  
pp. 2671
Author(s):  
AB Manas ◽  
RAJ Smith ◽  
J Simpson
Keyword(s):  
Conformational Analysis ◽  
Dihedral Angle ◽  
Spin System ◽  
Title Compound ◽  
Second Order ◽  
Coupling Constants ◽  
X Ray ◽  
Unsaturated Ketones ◽  
Iterative Analysis ◽  
Related Compounds

Iterative analysis of the second-order ABX spin system in the 1H n.m.r. of the title compound gave coupling constants which are consistent with a conformation involving a H-C-C-H dihedral angle of about 90�. The structure was confirmed by X-ray analysis. The 1H n.m.r. of the related compounds 2,2-dimethyl-5-pheny1-6,6,6-tri(phenylthio)hexan-3-one and 1,3-diphenyl-4,4,4-tri(pheny1-thio)butan-1-one were also analysed and found to have similar conformational characteristics.

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