Synthesis of 3,3,5,5-tetrabenzyl-1,2,4-trithiol and 1,2-dis(1,3-arylpropan-2-yl)disulfane

Fu Feng Meng Huang Zheng-Chao Duan Wei-Bing Hu

Citation:  Fu Feng, Meng Huang, Zheng-Chao Duan, Wei-Bing Hu. Synthesis of 3,3,5,5-tetrabenzyl-1,2,4-trithiol and 1,2-dis(1,3-arylpropan-2-yl)disulfane[J]. Chinese Chemical Letters, 2013, 24(10): 909-911. shu

Synthesis of 3,3,5,5-tetrabenzyl-1,2,4-trithiol and 1,2-dis(1,3-arylpropan-2-yl)disulfane

    通讯作者: Wei-Bing Hu,
  • 基金项目:

    We are grateful for the Natural Science Foundation of Hubei Province (No. 2012FFB01103) (No. 2012FFB01103)

    the Hubei Provincial Department of Education (No. Q20131905) (No. Q20131905)

    the National Natural Science Foundation of China (No. 21262011) (No. 21262011)

    the Fund of Ethnic Affairs Commission of China (No. 12HBZ010). (No. 12HBZ010)

摘要: Novel sulfur-containing compounds (3a-3c, 4a-4c) were obtained in ethanol with 1,3-diphenyl-2-propanone as the starting material. The advantages of this procedure were mild reaction conditions, simple protocol, and high yields. The structures of the products were characterized by IR, 1H NMR, MS and elementary analysis. The crystal of the new compound 4a belongs to monoclinic, space group C2 with a = 18.727(3), b = 6.5179(9), c = 13.7576(18)Å, β = 131.0610(10)°, V = 1266.2(3)Å3, Z = 2, Dc = 2.136 g/cm3, μ = 1.078 mm-1, F(0 0 0) = 843, R = 0.0490 and wR = 0.1247 for 3211 observed reflection with I > 2σ(I). X-ray analysis reveals that the molecule is not symmetrical, the molecular structure is stabilized by weak π-π stacking interactions, and no classical hydrogen bonds can be observed.

English

  • 
    1. [1] J.M. Khurana, K.S. Prabhat, Chemoselective alkylation of thiols: a detailed investingation of reactions of thiols with halides, Synth. Commun. 22 (1992) 1691-1702.[1] J.M. Khurana, K.S. Prabhat, Chemoselective alkylation of thiols: a detailed investingation of reactions of thiols with halides, Synth. Commun. 22 (1992) 1691-1702.

    2. [2] E.S. Paul, Inorganic halide salt catalysts for hydroxyalkylation of phenols or thiophenols, US 4341905, 1982.[2] E.S. Paul, Inorganic halide salt catalysts for hydroxyalkylation of phenols or thiophenols, US 4341905, 1982.

    3. [3] I. Katz, W.J. Evers, A.S. Highlands, Flavoring compositions and processesutilizing alpha-ketothiols, US 3773524, 1973.[3] I. Katz, W.J. Evers, A.S. Highlands, Flavoring compositions and processesutilizing alpha-ketothiols, US 3773524, 1973.

    4. [4] W.J. Evers, H.H. Heinsohn, F.L. Schmitt, alpha-Oxy(oxo)mercaptan perfume and cologne compositions, US 4070308, 1978.[4] W.J. Evers, H.H. Heinsohn, F.L. Schmitt, alpha-Oxy(oxo)mercaptan perfume and cologne compositions, US 4070308, 1978.

    5. [5] D. Craig, K. Daniels, Additive pummerer reactions of vinylic sulphoxides. Synthesis of 2-(phenylsulphenyl) aldehydes and primary alcohols, Tetrahedron Lett. 32 (1991) 6973-6976.[5] D. Craig, K. Daniels, Additive pummerer reactions of vinylic sulphoxides. Synthesis of 2-(phenylsulphenyl) aldehydes and primary alcohols, Tetrahedron Lett. 32 (1991) 6973-6976.

    6. [6] F. Feng, W.B. Hu, H.X. Liu, Study on synthesis of 1, 3-diphenyl-2,2-dithiol, J. Hubei Inst. Nationalities 24 (2006) 69-70.[6] F. Feng, W.B. Hu, H.X. Liu, Study on synthesis of 1, 3-diphenyl-2,2-dithiol, J. Hubei Inst. Nationalities 24 (2006) 69-70.

    7. [7] G.M. Sheldrick, SHELXS-97, Program for Crystal Structure Solution, University of Göttingen, 1990.[7] G.M. Sheldrick, SHELXS-97, Program for Crystal Structure Solution, University of Göttingen, 1990.

    8. [8] G.M. Sheldrick, SHELXL-97, Program for Crystal Structure Refinement, University of Göttingen, 1997.[8] G.M. Sheldrick, SHELXL-97, Program for Crystal Structure Refinement, University of Göttingen, 1997.

    9. [9] F. Feng, Solvent-free Michael addition reaction of fluorene with chalcon, Chin. Chem. Lett. 22 (2011) 29-32.[9] F. Feng, Solvent-free Michael addition reaction of fluorene with chalcon, Chin. Chem. Lett. 22 (2011) 29-32.

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  • 收稿日期:  2013-03-04
  • 网络出版日期:  2013-05-08
通讯作者: 陈斌, bchen63@163.com
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