2000
DOI: 10.1002/(sici)1521-3773(20000502)39:9<1669::aid-anie1669>3.0.co;2-6
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Reaction of Organic Selenocyanates with Hydroxides: The One-Pot Synthesis of Dialkyl Diselenides from Alkyl Bromides

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Cited by 69 publications
(44 citation statements)
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“…To gain more insights, some control experiments were conducted (Scheme ). Treatment of selenocyanatobenzene with KOH could afford PhSeSePh in 92% yield (Scheme , a ) . To confirm that KOH indeed promoted the monofluoromethylation, we performed a reaction with PhSeSePh and ICFH 2 in the absence of KOH.…”
Section: Figuresupporting
confidence: 76%
“…To gain more insights, some control experiments were conducted (Scheme ). Treatment of selenocyanatobenzene with KOH could afford PhSeSePh in 92% yield (Scheme , a ) . To confirm that KOH indeed promoted the monofluoromethylation, we performed a reaction with PhSeSePh and ICFH 2 in the absence of KOH.…”
Section: Figuresupporting
confidence: 76%
“…We adapted the procedures described by Krief 25 and Plano 26 to prepare and structurally characterize [ p ‐H 2 NC 6 H 4 Se] 2 . The [ p ‐H 2 NC 6 H 4 Se] – group is a versatile building block containing hard and soft donors.…”
Section: Resultsmentioning
confidence: 62%
“…Several methods have been described for the synthesis of diorganoyl diselenides and ditellurides [9][10][11][12][13][14][15][16][17][18] which include the reaction of metal diselenides or ditellurides with organoylhalides [19][20][21], the well established reaction of Grignard reagents with elemental selenium or tellurium, the reduction of selenocyanates [22][23][24][25] and the oxidation of both selenols and selenolates [26,27]. Several methodologies have been described for the synthesis of diorganoyl disulfides generally obtained by oxidation of thiols [28][29][30][31][32][33] or even, according to Taniguchi, from elemental sulfur and aryl iodides catalyzed by Cu-bpy, aluminum and sodium carbonate [34].…”
Section: Introductionmentioning
confidence: 99%
“…61-62 • C), yield: 70%; 1 H NMR (CDCl 3 , 200 MHz) (ı, ppm) 7.61 (m, 4H), 7.25-7.21 (m, 6H); 13 C NMR (CDCl 3 , 50 MHz) (ı, ppm) 131.5, 130.9, 129.1, 127.7; GC-MS: m/z (%) 314(34), 312(33), 310(16), 234(18), 232(10), 230(5), 159(16), 158(25), 157 (80), 155(48), 153(22), 117(16), 78 (78), 77 (100), 51(61), 50(29).Bis(4-methylphenyl) diselenide (2b):[27,47] orange solid, mp 42-43 • C (lit. 44-45 • C), yield: 71%; 1 H NMR (CDCl 3 , 200 MHz) (ı, ppm) 7.49 (d, J = 8.2 Hz, 4H), 7.07 (d, J = 8.2 Hz, 4H), 2.34 (s, 6H); 13 C NMR (CDCl 3 , 50 MHz) (ı, ppm) 139.Bis(3-methoxyphenyl) diselenide (2d): [47] orange solid, mp 191-193 • C (lit.…”
mentioning
confidence: 99%