35479-41-5Relevant academic research and scientific papers
CONFIGURATION AND CONFORMATION OF 3,5-DIPHENYL-2-THIABICYCLO DECANE
Klimenko, S. K.,Stolbova, T. V.,Evtushenko, I. Ya.,Kharchenko, V. G.
, p. 1006 - 1009 (1981)
The PMR spectra of 3,5-diphenyl-2-thiabicyclodecane and its 4,6-dideuteroderivative and S-oxide in the presence of Eu(dpm)3were studied.It was established that 3,5-diphenyl-2-thiabicyclodecane has a cis, cis, cis configuration.The extremal spin-spin coupling constants (SSCC) constitute evidence for conformational rigidity of the investigated condensed system, which exists in the form of a puckered chair.The formation of the same cis, cis, cis isomer of 3,5-diphenyl-2-thiabicyclodecane in the case of catalytic hydrogenation, disproportionation with trifluoroacetic acid, and ionic hydrogenation constitutes evidence for stereospecificity of the processes involving the reduction of the double bonds in 2,4-diphenyl-5,6-tetramethylene-6H-thiopyran.
FORMATION OF 3,5-DIPHENYL-2-THIABICYCLODEC-Δ1,6-ENE UNDER THE CONDITIONS OF THE PUMMERER REACTION AND ITS STRUCTURE
Stolbova, T. V.,Klimenko, S. K.,Shcherbakov, A. A.,Aleksandrov, G. G.,Struchkov, Yu. T.,Kharchenko, V. G.
, p. 818 - 821 (1980)
The Pummerer rearrangement was investigated in the case of 3,5-diphenyl-2-thiabicyclodecane S-oxide.It is shown that, of the two possible isomers, this compound forms only 3,5-diphenyl-2-thiabicyclodec-Δ1,6-ene under the conditions of the Pummerer reaction; a secondary transformation, viz., disproportionation of the latter to 3,5-diphenyl-2-thiabicyclodecane and 2,4-diphenyl-5,6-tetramethylenethiopyrylium acetate, is observed. 3,5-Diphenyl-2-thiabicyclodec-Δ1,6-ene was subjected to an x-ray diffraction study; it was proved unambiguously that the C1=C6 double bond has a lenght of 1.335 Angstroem and that the dihydrothiopyran and cyclohexene rings have a distorted half-chair conformation: the dihedral angles between the phenyl rings and the planar fragment of the heteroring are 76.8 and 93.2 deg C.
STEREOCHEMICAL SPECIFICITY OF THE PALLADIUM-CATALYZED HYDROGENATION OF CYCLOHEXATHIOPYRANS AND THEIR DERIVATIVES
Klimenko, S. K.,Tyrina, T. I.,Sorokin, N. N.
, p. 506 - 512 (2007/10/02)
Conformationally and configurationally homogenous 2α-R1-4α-R2-cis-1-thiadecalins with an equatorial orientation of the substituents attached to the C(2) and C(4) atoms were isolated as the final reduction produc
CONFIGURATIONALLY AND CONFORMATIONALLY HOMOGENEOUS ARYL-cis-1-THIADECALINS
Klimenko, S. K.,Stolbova, T. V.,Tyrina, T. I.,Sorokin, N. N.,Leshcheva, I. F.,et al.
, p. 728 - 733 (2007/10/02)
The structure of aryl-substituted cis-1-thiadecalins formed together with 5,6-tetramethylenethiopyrylium salts in disproportionation reactions of condensed 4H-, 6H-thiopyrans and dihydrothiopyrans with CF3COOH, as well as in the ionic reduction of the latter by the ion pair trifluoroacetic acid-triethylsilane, was studied.It was shown that the reduction proceeds stereospecifically with the formation of configurationally and conformationally homogeneous aryl-cis-1-thiadecalins possessing 2α-R1- and 2α-R1-4α-R2-configurations.The configurational and conformational assignments were made by the 13C NMR method.
Disproportionation of condensed thiopyrans with trifluoroacetic and deuterotrifluoroacetic acids
Klimenko,Stolbova,Kharchenko
, p. 998 - 1001 (2007/10/02)
The disproportionation of isomeric 2,4-diphenyl-5,6-tetramethylene-4H-thiopyran,-6H-thiopyran, and 2,4-diphenyl-5,6,7,9-tetrahydrothiochromene with trifluoroacetic and deuterotrifluoroacetic acids was investigated for the first time. The direction of protonation of the sulfides was established, and this made it possible to form a judgment regarding the structure of the intermediate carbonium ions, which are hydride-ion acceptors. The correctness of the mechanism of disproportionation of condensed two-ring sulfides with a 4H-thiopyran ring was proved. A mechanism for the disproportionation of isomeric 2,4-diphenyl-5,6-tetramethyl-6H-thiopyran and 2,4-dipheny1-5,6,7,9-tetrahydrothiochromene was proposed.
CATALYTIC REDUCTION OF THIOPYRYLIUM SALTS AND THEIR CONDENSED ANALOGS
Kharchenko, V. G.,Bozhenova, O. A.,Shebaldova, A. D.
, p. 2158 - 2162 (2007/10/02)
A method was developed for the synthesis of substituted thiacyclohexanes, thiadecalins, and perhydrothioxanthenes by reduction of thiopyrylium salts and their condensed analogs under the conditions of catalytic hydrogenation in the presence of catalysts b
REACTIONS OF "SEMICYCLIC" 1,5-DIKETONES WITH HYDROGEN SULFIDE AND TRIFLUOROACETIC ACID
Stolbova, T. V.,Klimenko, S. K.,Kharchenko, V. G.
, p. 170 - 173 (2007/10/02)
The reactions of known and new "semicyclic" 1,5-diketones with hydrogen sulfide and with trifluoroacetic acid were studied.It was shown that under the investigated conditions both 1-aryl- and 1,3-diaryl-substituted diketones form 3R-5R-2-thiabicycloalkane
