View source for Chemistry:Naphthalen-1,8-diyl 1,3,2,4-dithiadiphosphetane 2,4-disulfide

{{Chembox
| Verifiedfields = changed
| verifiedrevid = 462258463
| Name = Naphthalen-1,8-diyl 1,3,2,4-<br />
dithiadiphosphetane 2,4-disulfide
| ImageFileL1 = Np2P2S4-2D-skeletal.png
| ImageNameL1 = Wireframe model of naphthalen-1,8-diyl 1,3,2,4-dithiadiphosphetane 2,4-disulfide
| ImageFileR1 = Np2P2S4-3D-balls.png
| ImageNameR1 = Ball and stick model of naphthalen-1,8-diyl 1,3,2,4-dithiadiphosphetane 2,4-disulfide
| PIN = Naphthalen-1,8-diyl 1,3,2,4-dithiadiphosphetane<br />
2,4-disulfide
| SystematicName = 3,14-Dithia-2λ<sup>5</sup>,4λ<sup>5</sup>-diphosphatetracyclo[7.3.1.<br />
1<sup>2,4</sup>.0<sup>5,13</sup>]tetradeca-1(12),5,7,9(13),10-<br />
pentaene-2,4-dithione
|Section1={{Chembox Identifiers
| CASNo = 115505-46-9
| CASNo_Ref = {{Cascite|changed|CAS}}
| PubChem = 11243996
| InChIKey1 = NYHOAPMWYNAQJE-UHFFFAOYSA-N
| ChemSpiderID = 9419032
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| 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
| InChI1 = 1S/C10H6P2S4/c13-11-8-5-1-3-7-4-2-6-9(10(7)8)12(14,15-11)16-11/h1-6H
| SMILES = S=P13SP(=S)(S1)c4c2c(cccc23)ccc4
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C10H6P2S4/c13-11-8-5-1-3-<br />
7-4-2-6-9(10(7)8)12(14,15-11)<br />
16-11/h1-6H
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = NYHOAPMWYNAQJE-UHFFF<br />
AOYSA-N}}
|Section2={{Chembox Properties
| Formula = C<sub>10</sub>H<sub>6</sub>P<sub>2</sub>S<sub>4</sub>
| MolarMass = 316.36 g mol<sup>−1</sup>
| Appearance = 
| Density = 
| MeltingPt = 
| BoilingPt = 
| Solubility = 
  }}
|Section3={{Chembox Hazards
| MainHazards = 
| FlashPt = 
| AutoignitionPt = 
  }}
}}

A compound related to [[Chemistry:Lawesson's reagent|Lawesson's reagent]] named '''NpP<sub>2</sub>S<sub>4</sub>''' has been formed by the reaction of 1-bromo[[Chemistry:Naphthalene|naphthalene]] with P<sub>4</sub>S<sub>10</sub>, this is a 1,3,2,4-dithiadiphosphetane 2,4-disulfide which has a naphth-1,8-diyl group holding the two [[Chemistry:Phosphorus|phosphorus]] atoms together. The mechanism by which the NpP<sub>2</sub>S<sub>4</sub> forms is unclear, but it is thought to occur through some [[Biology:Radical|free radical]] process, and [[Chemistry:Naphthalene|naphthalene]] has been detected as a side product in its synthesis. In general NpP<sub>2</sub>S<sub>4</sub> has been found to be less reactive than Lawesson's reagent, this result agrees with the [[Hypothesis|hypothesis]] that the dithiophosphine [[Chemistry:Ylide|ylide]]s are responsible for the majority of the chemical reactions of the 1,3,2,4-dithiadiphosphetane 2,4-disulfides.

It has been found that NpP<sub>2</sub>S<sub>4</sub> reacts with many hydroxyl compounds, for instance [[Chemistry:Methanol|methanol]], [[Chemistry:Ethylene glycol|ethylene glycol]] and a [[Chemistry:Catechol|catechol]] to form species with [[Chemistry:Oxygen|oxygen]] atoms bonded to the phosphorus atoms.

Methanol reacts to form compound which has one O-methyl and one S-methyl bonded to the two phosphorus atoms. 

{|align="center"  class="wikitable" style="width:500px"
|<div  style="text-align: center;">[[Image:Npmethanol.jpg|150px|The structure of the product of methanol and NpP<sub>2</sub>S<sub>4</sub>]]</div>||<div  style="text-align: center;">150px|The structure of the first product of NpP<sub>2</sub>S<sub>4</sub> with ethylene glycol</div>||<div  style="text-align: center;">[[Image:Npcate.jpg|150px|The structure of the product of di-tert-butylcatechol with NpP<sub>2</sub>S<sub>4</sub>]]</div>
|-
|<div  style="text-align: center;">The structure of the product of methanol and NpP<sub>2</sub>S<sub>4</sub></div>||<div  style="text-align: center;">The structure of the first product of NpP<sub>2</sub>S<sub>4</sub> with ethylene glycol</div>||<div  style="text-align: center;">The structure of the product of di-tert-butylcatechol with NpP<sub>2</sub>S<sub>4</sub></div>
|}

{{DEFAULTSORT:Naphthalen-1,8-Diyl 1,3,2,4-Dithiadiphosphetane 2,4-Disulfide}}
[[Category:Reagents for organic chemistry]]
[[Category:Organosulfur compounds]]
[[Category:Naphthalenes]]

{{Unreferenced|date=2021}}
{{Sourceattribution|Naphthalen-1,8-diyl 1,3,2,4-dithiadiphosphetane 2,4-disulfide}}