BINOL aza macrocycle derivatives: Synthesis of dinaphthosulfone aza macrocycles using p-toluenesulfonic acid (p-TsOH) in methanol as an efficient route and evaluation of their 1H NMR spectra

Phosphorus, Sulfur and Silicon and the Related Elements

Volumn 184, Issue 8, 2009, Pages 2066-2077

  Rostami, Esmael ^a   Shockravi, Abbas ^b   Fattahi, Hanif ^b   Heydarian, Davood ^b   Minaee, Shima Shahbanzadeh ^b   Naghdi, Shaghayegh ^b   Lotf, Ebrahim Abouzari ^b   Sadeghpour, Mahdieh ^b   Hosseini, Hamideh ^b   Taheri, Zahra ^b   Ghorbani, Shahla ^b   Javadi, Ali ^b   Ataei, Shahram Mehdipoure ^c  

^a Bushehr Payamenoor University   (Iran)

^b KHARAZMI UNIVERSITY   (Iran)

^c IRAN POLYMER AND PETROCHEMICAL INSTITUTE   (Iran)

Author keywords

1H NMR; Aza thia macrocycle; BINOL; Dinaphthosulfone; Synthesis

Indexed keywords

EID: 70449555556     PISSN: 10426507     EISSN: 15635325     Source Type: Journal    
DOI: 10.1080/10426500802421036     Document Type: Article

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30. Synthesis of 1,1--thiobis-(2-naphthoxy(2-methyl acetate)) (2): To a mixture of 1 (6.04 g, 19 mmol), potassium carbonate (5.24 g, 38 mmol), and potassium iodide (catalytic) in acetonitrile (100 mL) at room temperature, methylchloroacetate (3.35 mL, 38 mmol) was added. Then the reaction mixture was refluxed for 24 h. After completion of the reaction (TLC), the mixture was cooled to room temperature, water was added and extracted with chloroform (3 × 50 mL). The mixture was washed with sodium hydroxide solution (10%), dried, and evaporated to afford a precipitate that recrystallized from ethanol, to give pure 2 in 91% yield. Mp 126.5-127?C; IR (KBr): 3040, 3000, 2970, 1750, 1595, 1500, 1450, 1300, 1250,1200, 1090, 1040, 810, 750 cm-1;1H NMR (300 MHz, acetone-d6)): ä = 3.65 (s, 6H, CH3), 4.65 (s, 4H, CH2), 7.09 (ddd, J = 1.32, 6.94, 8.46 Hz, 2H, Ar), 7.26 (d, J = 9.05 Hz, 2H, Ar ), 7.35 (ddd, J = 1.11, 6.84, 7.98 Hz, 2H, Ar), 7.81 (d, J = 7.91 Hz, 2H, Ar), 7.83 (d, 2H, J = 9.02 Hz, Ar), 8.69 (d, 2H, J = 8.59 Hz, Ar) ppm; MS (EI) m/z (%) = 462 (43), 316 (4), 300 (36), 283 (12), 268 (7), 248 (11), 216 (63), 187 (44), 144 (23), 127 (40), 115 (100), 102 (14), 99 (18), 69 (5), 63 (19), 45 (73); Anal. Calcd. for C26H22O6S (462.11): C, 67.52; H, 4.79. Found: C, 67.45; H, 4.67.
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