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| verifiedrevid = 402002226 |
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|verifiedrevid = 408397915 |
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| Name = Diphenyl diselenide |
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| ImageFile = Diphenyl diselenide.png |
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|Name = Diphenyl diselenide |
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|ImageFile = Diphenyldiselenide.svg |
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|ImageSize = 120 |
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| ImageName = Chemical structure of diphenyl diselenide |
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| IUPACName = Diphenyl diselenide |
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|ImageName = Chemical structure of diphenyl diselenide |
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| OtherNames = Phenyl diselenide |
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|ImageFile1 = Diphenyl-diselenide-from-xtal-2010-Mercury-3D-sf.png |
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|ImageSize1 = 210 |
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| Section1 = {{Chembox Identifiers |
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|ImageName1 = Space-filling model |
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| SMILES = c1ccc(cc1)c2ccccc2 |
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|IUPACName = 1,1′-Diselanediyldibenzene |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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|OtherNames = Phenyl diselenide |
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| ChemSpiderID = 14710 |
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|Section1={{Chembox Identifiers |
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| PubChem = 15460 |
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|SMILES = c1ccc(cc1)c2ccccc2 |
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| InChI = 1/C12H10Se2/c1-3-7-11(8-4-1)13-14-12-9-5-2-6-10-12/h1-10H |
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|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| InChIKey = YWWZCHLUQSHMCL-UHFFFAOYAK |
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|ChemSpiderID = 14710 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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|EC_number = 216-780-2 |
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| StdInChI = 1S/C12H10Se2/c1-3-7-11(8-4-1)13-14-12-9-5-2-6-10-12/h1-10H |
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|PubChem = 15460 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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|InChI = 1/C12H10Se2/c1-3-7-11(8-4-1)13-14-12-9-5-2-6-10-12/h1-10H |
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| StdInChIKey = YWWZCHLUQSHMCL-UHFFFAOYSA-N |
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|InChIKey = YWWZCHLUQSHMCL-UHFFFAOYAK |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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|StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| CASNo = 1666-13-3 |
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|StdInChI = 1S/C12H10Se2/c1-3-7-11(8-4-1)13-14-12-9-5-2-6-10-12/h1-10H |
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| RTECS = JM9152500 |
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|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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}} |
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|StdInChIKey = YWWZCHLUQSHMCL-UHFFFAOYSA-N |
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| Section2 = {{Chembox Properties |
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|CASNo_Ref = {{cascite|correct|CAS}} |
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| Formula = C<sub>12</sub>H<sub>10</sub>Se<sub>2</sub> |
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| MolarMass = 312.13 g/mol |
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|CASNo = 1666-13-3 |
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|UNII_Ref = {{fdacite|correct|FDA}} |
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| Appearance = Orange powder |
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|UNII = 9ATU3Z459Q |
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| Density = 1.84 g/cm<sup>3</sup> |
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|RTECS = JM9152500 |
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| Solubility = Insoluble |
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| Solvent = other solvents |
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|Section2={{Chembox Properties |
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| SolubleOther = ] |
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|C=12 | H=10 | Se=2 |
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| MeltingPt = 59-61 °C |
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|Appearance =Yellow crystals |
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| BoilingPt = °C |
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|Density = 1.84 g/cm<sup>3</sup> |
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|Solubility = Insoluble |
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| Section3 = {{Chembox Structure |
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|Solvent = other solvents |
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| Coordination = 90° at Se<br />C<sub>2</sub> symmetry |
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|SolubleOther = ], ], hot ] |
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| Dipole = 0 ] |
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|MeltingPtC = 59 to 61 |
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| Section7 = {{Chembox Hazards |
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|Section3={{Chembox Structure |
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| ExternalMSDS = |
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|Coordination = 90° at Se{{citation needed|date=November 2011}}<br/>C<sub>2</sub> symmetry{{citation needed|date=November 2011}} |
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| MainHazards = Toxic |
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|Dipole = 0 ] |
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| RPhrases = 23/25-33-50/53 |
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| SPhrases = 20/21-28-45-60-61 |
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|Section4={{Chembox Hazards |
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|GHSPictograms = {{GHS06}}{{GHS08}}{{GHS09}} |
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| Section8 = {{Chembox Related |
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|GHSSignalWord = Danger |
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| OtherCpds = ],<br />] |
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|HPhrases = {{H-phrases|301|331|373|410}} |
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|PPhrases = {{P-phrases|260|261|264|270|271|273|301+310|304+340|311|314|321|330|391|403+233|405|501}} |
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|Section5={{Chembox Related |
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|OtherCompounds = ],<br />] |
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'''Diphenyl diselenide''' is the ] with the formula (C<sub>6</sub>H<sub>5</sub>)<sub>2</sub>Se<sub>2</sub>, abbreviated ]<sub>2</sub>Se<sub>2</sub> This orange-coloured solid is the oxidized derivative of ]. It is used as a source of the PhSe unit in ]. |
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'''Diphenyl diselenide''' is the ] with the formula (C<sub>6</sub>H<sub>5</sub>)<sub>2</sub>Se<sub>2</sub>, abbreviated ]<sub>2</sub>Se<sub>2</sub>. This yellow-coloured solid is the oxidized derivative of ]. It is used as a source of the PhSe unit in ]. |
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== Preparation and properties == |
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Ph<sub>2</sub>Se<sub>2</sub> is prepared by the oxidation of benzeneselenoate, which is generated via the ]:<ref>{{OrgSynth |author=Reich, H. J.; Cohen, M. L.; Clark, P. S. |year=1979|title=Reagents for Synthesis of Organoselenium Compounds: Diphenyl Diselenide and Benzeneselenenyl Chloride |volume=59 |pages=141 |collvol=6 |collvolpages=533 |prep=CV6P0533}}</ref> |
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Ph<sub>2</sub>Se<sub>2</sub> is prepared by the oxidation of benzeneselenoate, the conjugate base of benzeneselenol which is generated via the ]:<ref>{{OrgSynth | author = Reich, H. J. | author2 = Cohen, M. L. | author3 = Clark, P. S. | title = Reagents for Synthesis of Organoselenium Compounds: Diphenyl Diselenide and Benzeneselenenyl Chloride | year = 1979 | volume = 59 | pages = 141 | collvol = 6 | collvolpages = 533 | prep = CV6P0533}}</ref> |
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:] + Se → PhSeMgBr |
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:] + Se → PhSeMgBr |
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:2 PhSeMgBr + Br<sub>2</sub> → Ph<sub>2</sub>Se<sub>2</sub> + 2 ] |
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:2 PhSeMgBr + Br<sub>2</sub> → Ph<sub>2</sub>Se<sub>2</sub> + 2 ] |
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It has a centrosymmetric structure, with an Se-Se bond length of 2.29 A.<ref>Marsh, R. E. "The Crystal Structure of Diphenyl Diselenide" Acta Crystallographica (1952), volume 5, pages 458-462. doi:10.1107/S0365110X52001349.</ref> |
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The molecule has idealized C<sub>2</sub>-symmetry, like hydrogen peroxide and related molecules. The Se-Se bond length of 2.29 Å the C-Se-Se-C dihedral angle is 82° and the C-Se-Se angles are near 110°.<ref>{{Cite journal | last1 = Marsh | first1 = R. E. | title = The Crystal Structure of Diphenyl Diselenide | doi = 10.1107/S0365110X52001349 | journal = Acta Crystallographica | volume = 5 | issue = 4 | pages = 458–462 | year = 1952 | doi-access = free}}</ref> |
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== Medical applications == |
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Diphenyl diselenide alleviates ] poisoning in ].<ref>{{Cite journal|last1=Baldissera|first1=Matheus D.|last2=Souza|first2=Carine F.|last3=da Silva|first3=Aleksandro S.|last4=Henn|first4=Alessandra S.|last5=Flores|first5=Erico M. M.|last6=Baldisserotto|first6=Bernardo|year=2020|title=Diphenyl diselenide dietary supplementation alleviates behavior impairment and brain damage in grass carp (Ctenopharyngodon idella) exposed to methylmercury chloride|journal=Comparative Biochemistry and Physiology. Toxicology & Pharmacology|volume=229|pages=108674|doi=10.1016/j.cbpc.2019.108674|issn=1532-0456|pmid=31760078|s2cid=208274623}}</ref> |
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==Reactions== |
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==Reactions== |
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Two reactions characteristic of Ph<sub>2</sub>Se<sub>2</sub> are reduction and chlorination: |
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A reaction characteristic of Ph<sub>2</sub>Se<sub>2</sub> is its reduction: |
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:Ph<sub>2</sub>Se<sub>2</sub> + 2 Na → 2 PhSeNa |
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:Ph<sub>2</sub>Se<sub>2</sub> + 2 Na → 2 PhSeNa |
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:Ph<sub>2</sub>Se<sub>2</sub> + Cl<sub>2</sub> → 2 PhSeCl |
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PhSeNa is a useful nucleophile, and can be used to introduce the phenylselenyl group by ] of ], alkyl sulfonates (]ates or ]ates) or ]s. The example below was taken from a synthesis of morphine.<ref>Taber, D. F.; Neubert, T. B.; Rheingold, A. L. ''J. Am. Chem. Soc.'' '''2002''', ''124'', 12416<!--<a href="http://dx.doi.org/10.1021/ja027882h">DOI</a> --></ref> |
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PhSeNa is a useful nucleophile used to introduce the phenylselenyl group by ] of ], alkyl sulfonates (]ates or ]ates) and ]s. The example below was taken from a synthesis of morphine.<ref>{{Cite journal | last1 = Taber | first1 = D. F. | last2 = Neubert | first2 = T. D. | last3 = Rheingold | first3 = A. L. | doi = 10.1021/ja027882h | title = Synthesis of (−)-Morphine | journal = Journal of the American Chemical Society | volume = 124 | issue = 42 | pages = 12416–12417 | year = 2002 | pmid = 12381175}}</ref> |
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:] |
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Another characteristic reaction is ]: |
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PhSeCl is a powerful electrophile, used to introduce PhSe groups by reaction with a variety of nucleophiles, including ], ], ]s, ]s, ]s and ]s. In the sequence below (early steps in the synthesis of Strychnofoline), a PhSe group is introduced by reaction of a ] enolate with PhSeCl.<ref>Lerchner, A.; Carreira, E. M. ''J. Am. Chem. Soc.'' '''2002''', ''124'', 14826</ref> This sequence is a powerful method for the conversion of ]s to their α,β-unsaturated analogs.<ref>''Preparation of α,β-Unsaturated Carbonyl Compounds and Nitriles by Selenoxide Elimination.'' Reich, H. J.; Wollowitz, S. ''Organic Reactions'' '''1993''', ''44'', 1.</ref> |
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:Ph<sub>2</sub>Se<sub>2</sub> + Cl<sub>2</sub> → 2 PhSeCl |
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PhSeCl is a powerful electrophile, used to introduce PhSe groups by reaction with a variety of nucleophiles, including ], ], ]s, ]s, ]s and ]s. In the sequence below (early steps in the synthesis of Strychnofoline), a PhSe group is introduced by reaction of a ] enolate with PhSeCl.<ref>{{cite journal |author1=Lerchner, A. |author2=Carreira, E. M. | title = First Total Synthesis of (±)-Strychnofoline via a Highly Selective Ring-Expansion Reaction | journal = ] | year = 2002 | volume = 124 | issue = 50 | pages = 14826–14827 | doi = 10.1021/ja027906k |pmid=12475306}}</ref> This sequence is a powerful method for the conversion of ]s to their α,β-unsaturated analogs.<ref>{{cite journal | title = Preparation of α,β-Unsaturated Carbonyl Compounds and Nitriles by Selenoxide Elimination |author1=Reich, H. J. |author2=Wollowitz, S. | journal = ] | year = 1993 | volume = 44 | pages = 1–296 | doi = 10.1002/0471264180.or044.01 |isbn=0471264180}}</ref> |
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Diphenyl diselenide itself is also a source of a weakly electrophilic PhSe group in reactions with relatively powerful nucleophiles like Grignard reagents, lithium reagents and ester enolates (but not ketone enolates or weaker nucleophiles). PhSeCl is both more reactive, and more efficient, since with Ph<sub>2</sub>Se<sub>2</sub> half of the selenium is wasted. |
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Diphenyl diselenide itself is also a source of a weakly electrophilic PhSe group in reactions with relatively powerful nucleophiles like Grignard reagents, lithium reagents and ester enolates (but not ketone enolates or weaker nucleophiles). PhSeCl is both more reactive, and more efficient, since with Ph<sub>2</sub>Se<sub>2</sub> half of the selenium is wasted. |
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:Ph<sub>2</sub>Se<sub>2</sub> + Nu<sup>−</sup> → PhSeNu + PhSe<sup>−</sup> |
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:Ph<sub>2</sub>Se<sub>2</sub> + Nu<sup>−</sup> → PhSeNu + PhSe<sup>−</sup> |
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N-Phenylselenophtalimide (N-PSP) can be used if PhSeCl is too strong and diphenyl diselenide is too weak or wasteful.<ref>{{cite journal |last=Barrero |first=Alejandro F. |coauthors=E. J. Alvarez-Manzaneda, R. Chahboun, M. Corttés, V. Armstrong |year=1999 |title=Synthesis and antitumor activity of puupehedione and related compounds |journal=] |volume=55 |issue=52 |pages=15181–15208 | doi=10.1016/S0040-4020(99)00992-8 }}</ref> |
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''N''-Phenylselenophthalimide (N-PSP) can be used if PhSeCl is too strong and diphenyl diselenide is too weak or wasteful.<ref>{{cite journal | last = Barrero | first = A. F. |author2=Alvarez-Manzaneda, E. J. |author3=Chahboun, R. |author4=Corttés, M. |author5=Armstrong, V. | title = Synthesis and Antitumor Activity of Puupehedione and Related Compounds | journal = ] | year = 1999 | volume = 55 | issue = 52 | pages = 15181–15208 | doi = 10.1016/S0040-4020(99)00992-8}}</ref> |
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==Safety== |
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Organoselenium compounds are toxic. |
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==References== |
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==References== |
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{{Reflist}} |
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<references/> |
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{{DEFAULTSORT:Diphenyl Diselenide}} |
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