6160-65-2 Usage
Chemical Properties
yellow powder
Uses
Different sources of media describe the Uses of 6160-65-2 differently. You can refer to the following data:
1. 1,1’Thiocarbonyldiimidazole can be used to deoxygenate carboxylic monosaccharide analogues.
2. 1,1'-Thiocarbonyldiimidazole is used as a reagent for the deoxygenation of alcohols with tributyltin hydride and diols with lithium aluminum hydride. It is also used to deoxygenate carboxylic monosaccharide analogues. Further, it is a useful reagent involved in biochemical synthesis. In addition to this, it is used to prepare 1-[bis-(4-methoxy-phenyl)-methyl]-1H-imidazole by reacting with 4,4'-dimethoxy-benzhydrol.
Application
1,1′-Thiocarbonyldiimidazole (TCDI) is generally used as a reagent to carry out the deoxygenation of vicinal diols by forming cyclic thionocarbonate in Corey-Winter alkene synthesis.It is used as a reagent in the enantioselective total synthesis of (+)-hapalindole Q, 12-epi-fischerindole U and welwitindolinone A.It is also used in the preparation of trithiocarbonates, xanthates, and dithiocarbamates as chain transfer agents for the reversible addition fragmentation chain transfer and macromolecular design (RAFT/ MADIX) polymerization.
Synthesis Reference(s)
The Journal of Organic Chemistry, 43, p. 337, 1978 DOI: 10.1021/jo00396a035
Purification Methods
It forms yellow crystals on recrystallisation from tetrahydrofuran or by sublimation at 10-3torr (bath temperature 70-80o). It is hydrolysed by H2O and should be stored dry. [Staab & Walther Justus Liebigs Ann Chem 657 98 1962; Pullukat et al. Tetrahedron Lett 1953 1967, Hanessian et al. Can J Chem 65 1859 1987, Rajanbabu et al. J Am Chem Soc 111 1759 1989.] Thiochrome {2,7-dimethyl-5H -thiachromine-8-ethanol; 3,8-dimethyl-2-hydroxyethyl-5H -
Check Digit Verification of cas no
The CAS Registry Mumber 6160-65-2 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 6,1,6 and 0 respectively; the second part has 2 digits, 6 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 6160-65:
(6*6)+(5*1)+(4*6)+(3*0)+(2*6)+(1*5)=82
82 % 10 = 2
So 6160-65-2 is a valid CAS Registry Number.
6160-65-2Relevant articles and documents
Conversion of D-(-)-quinic acid into an enantiopure C-4 functionalized 2-iodocyclohexenone acetal
Su,Paquette
, p. 764 - 766 (1995)
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Origin of the "β-oxygen effect" in the Barton deoxygenation reaction
Crich, David,Beckwith, Athelstan L. J.,Chen, Chen,Yao, Qingwei,Davison, Ian G. E.,Longmore, Robert W.,De Parrodi, Cecilia Anaya,Quintero-Cortes, Leticia,Sandoval-Ramirez, Jésus
, p. 8757 - 8768 (2007/10/02)
Photolysis of O-neopentyl S-tributylstannyl dithiocarbonate with hexaphenyl distannane, and 4-methoxyacetophenone as sensitizer, results in crossover of the stannyl groups. The reaction of O-octyl O′-(2-butoxyethyl) thiocarbonate with tributyltin deuteride or tris(trimethylsilyl)silane and a radical initiator shows no significant preference for the cleavage of either C-O bond. Intermolecular competitions between O-octyl O′-phenyl thiocarbonate and O-(2-butoxyethyl) O′-phenyl thiocarbonate for a deficiency of stannane or silane also indicated no significant preference for reaction of the β-oxygen-substituted substrate, leading to the conclusion that in conformationally unrestricted systems there is no significant β-oxygen effect in the Barton deoxygenation reaction. Competition experiments between the cis- and trans-O-(4-phenylcyclohexyl) S-methyl dithiocarbonates and the cis- and trans-O-(2-phenyl1,3-dioxan-5-yl) S-methyl dithiocarbonates for reaction with tributylstannane reveal that in every case the heterocyclic system is more reactive. The cis-isomers of 4-phenylcyclohexyl S-methyl dithiocarbonate and O-(2-phenyl-1,3-dioxan-5-yl) 5-methyl dithiocarbonate, with their axial xanthates, are more reactive than the corresponding transisomers. Molecular mechanics calculations suggest that the greater reactivity of the cis-series with respect to the trans is due to the greater relief of strain on fragmentation.
