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Naphthalen-1,8-diyl 1,3,2,4-dithiadiphosphetane 2,4-disulfide

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Naphthalen-1,8-diyl 1,3,2,4-
dithiadiphosphetane 2,4-disulfide
Wireframe model of naphthalen-1,8-diyl 1,3,2,4-dithiadiphosphetane 2,4-disulfide
Wireframe model of naphthalen-1,8-diyl 1,3,2,4-dithiadiphosphetane 2,4-disulfide
Ball and stick model of naphthalen-1,8-diyl 1,3,2,4-dithiadiphosphetane 2,4-disulfide
Ball and stick model of naphthalen-1,8-diyl 1,3,2,4-dithiadiphosphetane 2,4-disulfide
Names
Preferred IUPAC name Naphthalen-1,8-diyl 1,3,2,4-dithiadiphosphetane
2,4-disulfide
Systematic IUPAC name 3,14-Dithia-2λ,4λ-diphosphatetracyclo[7.3.1.

1.0]tetradeca-1(12),5,7,9(13),10-

pentaene-2,4-dithione
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C10H6P2S4/c13-11-8-5-1-3-

    7-4-2-6-9(10(7)8)12(14,15-11)

    16-11/h1-6HKey: NYHOAPMWYNAQJE-UHFFF
    AOYSA-N
  • InChI=1S/C10H6P2S4/c13-11-8-5-1-3-7-4-2-6-9(10(7)8)12(14,15-11)16-11/h1-6H
  • InChI=1S/C10H6P2S4/c13-11-8-5-1-3-7-4-2-6-9(10(7)8)12(14,15-11)16-11/h1-6HKey: NYHOAPMWYNAQJE-UHFFFAOYSA-N
SMILES
  • S=P13SP(=S)(S1)c4c2c(cccc23)ccc4
Properties
Chemical formula C10H6P2S4
Molar mass 316.36 g mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

NpP2S4 is a compound related to Lawesson's reagent formed by the reaction of 1-bromonaphthalene with P4S10, this is a 1,3,2,4-dithiadiphosphetane 2,4-disulfide which has a naphth-1,8-diyl group holding the two phosphorus atoms together. The mechanism by which the NpP2S4 forms is not yet elucidated, but it is thought to occur by a process involving free radicals, and naphthalene has been detected as a side product in its synthesis. In general, NpP2S4 has been found to be less reactive than Lawesson's reagent, in agreement with the hypothesis that the dithiophosphine ylides are responsible for the majority of the chemical reactions of the 1,3,2,4-dithiadiphosphetane 2,4-disulfides.

NpP2S4 has been found to react with many hydroxyl compounds, such as methanol, ethylene glycol and a catechol to form species with oxygen atoms bonded to the phosphorus atoms.

NpP2S4 when refluxed in methanol reacts to form a heterocycle C12H12OP2S with one O-methyl and one S-methyl bonded to the two phosphorus atoms.

The structure of the product of methanol and NpP2S4 The structure of the first product of NpP2S4 with ethylene glycol The structure of the product of di-tert-butylcatechol with NpP2S4
The structure of the product of methanol and NpP2S4 The structure of the first product of NpP2S4 with ethylene glycol The structure of the product of di-tert-butylcatechol with NpP2S4

References

  1. ^ Eleftheriou, Maria-Elena; Novosad, Josef; Williams, David J.; Woollins, J. Derek (1991-01-01). "Reactions of 1,3-epithionaphtho[1,8-cd][1,2λ5,6λ5]thiadiphosphinine-1,3-dithione; the preparation and X-ray structure of NpP(S)(SMe)SP(S)(OMe), the first C3P2S ring". Journal of the Chemical Society, Chemical Communications (2): 116–117. doi:10.1039/C39910000116. ISSN 0022-4936.
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