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

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
Names
	Preferred IUPAC name Naphthalen-1,8-diyl 1,3,2,4-dithiadiphosphetane; 2,4-disulfide
	Systematic IUPAC name 3,14-Dithia-2λ5,4λ5-diphosphatetracyclo[7.3.1.; 12,4.05,13]tetradeca-1(12),5,7,9(13),10-; pentaene-2,4-dithione
Identifiers
CAS Number	115505-46-9 ;
3D model (JSmol)	Interactive image;
ChemSpider	9419032 ;
PubChem CID	11243996;
CompTox Dashboard (EPA)	DTXSID401027021 ;
	InChI InChI=1S/C10H6P2S4/c13-11-8-5-1-3-; 7-4-2-6-9(10(7)8)12(14,15-11); 16-11/h1-6H Key: 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/h1-6H Key: NYHOAPMWYNAQJE-UHFFFAOYSA-N;
	SMILES S=P13SP(=S)(S1)c4c2c(cccc23)ccc4;
Properties
Chemical formula	C10H6P2S4
Molar mass	316.36 g mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

NpP₂S₄ is a compound related to Lawesson's reagent formed by the reaction of 1-bromonaphthalene with P₄S₁₀,^[1] 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.^[1]


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

^ ^a ^b 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.

[:0-1] 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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