Journal of Organic Chemistry

, volume 64 , issue 12 , pages 4376-4380

Synthesis of sulfur-rich 1,2-and 1,3-dithiolo disulfides and thiodesaurines from diisopropyl sulfide

Charles W. Rees ¹

Oleg A. Rakitin ²

Carlos F Marcos ³

Tomás Torroba ⁴

Hide authors affiliations Show authors affiliations: 4 affiliations

Department of Chemistry, Imperial College of Science, Technology and Medicine, London, U.K. SW7 2AY |

N. D. Zelinsky Institute of Organic Chemistry, Academy of Sciences, Leninsky Prospect, 47, 117913 Moscow, Russia |

Departamento de Química Orgánica, Escuela Politécnica, Universidad de Extremadura, 10071 Cáceres, Spain |

⁴

Departamento de Química, Facultad de Ciencias, Universidad de Burgos, 09001 Burgos, Spain |

Publication type: Journal Article

Publication date: 1999-05-19

American Chemical Society (ACS)

Journal of Organic Chemistry

scimago Q2

wos Q1

SJR: 0.737

CiteScore: 6.1

Impact factor: 3.6

ISSN: 00223263, 15206904

DOI: 10.1021/jo9825005

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Organic Chemistry

Abstract

The reaction of diisopropyl sulfide and S2Cl2 in chlorobenzene, in the presence of DABCO, gives 4-isopropylthio-5-isopropyldithio-1,2-dithiole-3-thione (1) and the dimeric 5,5‘-dithiobis(4-isopropylthio-1,2-dithiol-3-thione) (2). If the reaction is performed in the presence of diisopropyl disulfide at the last stage of the reaction, disulfide 1 is selectively obtained. Some interconversions between 1 and 2 under UV irradiation are described, and a coherent set of reaction pathways for the formation of 1 and 2 are proposed. Treatment of 1 with DMAD in benzene gives the 1:1 adduct 9 in high yield; analogously the bisdithiolo disulfide 2 gives the 1:2 adduct 10, a very sulfur-rich molecule. Treatment of 1 with 1.27 equiv of triphenylphosphine in dichloromethane gives 4,5-di(isopropylthio)-1,2-dithiole-3-thione (11), but the treatment of 1 with 2 equiv of Ph3P affords thiodesaurine 12 (Z + E isomers), which was converted into desaurines 14 and 15 by treatment with nitrile oxide 16.

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Rees C. W. et al. Synthesis of sulfur-rich 1,2-and 1,3-dithiolo disulfides and thiodesaurines from diisopropyl sulfide // Journal of Organic Chemistry. 1999. Vol. 64. No. 12. pp. 4376-4380.

GOST all authors (up to 50) Copy

Rees C. W., Rakitin O. A., Marcos C. F., Torroba T. Synthesis of sulfur-rich 1,2-and 1,3-dithiolo disulfides and thiodesaurines from diisopropyl sulfide // Journal of Organic Chemistry. 1999. Vol. 64. No. 12. pp. 4376-4380.

RIS |

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RIS Copy

TY - JOUR

DO - 10.1021/jo9825005

UR - https://doi.org/10.1021/jo9825005

TI - Synthesis of sulfur-rich 1,2-and 1,3-dithiolo disulfides and thiodesaurines from diisopropyl sulfide

T2 - Journal of Organic Chemistry

AU - Rees, Charles W.

AU - Rakitin, Oleg A.

AU - Marcos, Carlos F

AU - Torroba, Tomás

PY - 1999

DA - 1999/05/19

PB - American Chemical Society (ACS)

SP - 4376-4380

IS - 12

VL - 64

SN - 0022-3263

SN - 1520-6904

ER -

BibTex |

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BibTex (up to 50 authors) Copy

@article{1999_Rees,

author = {Charles W. Rees and Oleg A. Rakitin and Carlos F Marcos and Tomás Torroba},

title = {Synthesis of sulfur-rich 1,2-and 1,3-dithiolo disulfides and thiodesaurines from diisopropyl sulfide},

journal = {Journal of Organic Chemistry},

year = {1999},

volume = {64},

publisher = {American Chemical Society (ACS)},

month = {may},

url = {https://doi.org/10.1021/jo9825005},

number = {12},

pages = {4376--4380},

doi = {10.1021/jo9825005}

}

MLA

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MLA Copy

Rees, Charles W., et al. “Synthesis of sulfur-rich 1,2-and 1,3-dithiolo disulfides and thiodesaurines from diisopropyl sulfide.” Journal of Organic Chemistry, vol. 64, no. 12, May. 1999, pp. 4376-4380. https://doi.org/10.1021/jo9825005.