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Synlett
Volumn , Issue 20, 2008, Pages 3172-3176
Regiodivergent approach to α- and β-(arylthio)alkenylphosphane oxides and sulfides: Aminophosphanes as synthetic auxiliaries
Author keywords

Alkynes; Aminophosphanes; Nucleophilic additions; Phosphorus; Regioselectivity
Indexed keywords

EID: 58149341743     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-0028-1087416     Document Type: Article
Times cited : (6)
References (31)
  • 18
    • 58149331584 scopus 로고    scopus 로고
    • Representative Experimental Procedure and Spectral Data for Compounds 3 A solution of P,P-diphenyl-P-phenylethynylphosphane oxide (1, 0.3 g, 1 mmol, 4-methoxythiophenol (0.21 g, 1.5 mmol, and KHMDS (0.5 M soln in toluene, 0.4 mL, 0.2 mmol) in toluene (20 mL) was refluxed for 12 h under a nitrogen atmosphere. Then the solvent was removed under reduced pressure, and the residue was purified by chromatography on deactivated silica gel (5% Et3N in hexane) with EtOAc-hexane 1:1 (v/v) and then EtOAc to yield a mixture of Z- and E-isomers; Rf, 0.5 (EtOAc, The subsequent fractional crystallization allowed the separation of the two isomers, Z)-P,P-Diphenyl -P-[2-phenyl-2-(4-methoxyphenylthio)]ethenylphosphane Oxide (Z-3b) White needles (from CH2Cl 2-Et2O, mp 196-197°C. IR Nujol, 1589, 1544, 1491, 1439, 1246, 11
    • 2PS (442.51): C, 73.28; H, 5.24. Found: C, 73.39; H, 5.38.
  • 20
    • 58149332540 scopus 로고    scopus 로고
    • Representative Experimental Procedure and Spectral Data for Compounds 6 A solution of P,P-diphenyl-P-phenylethynylphosphane oxide (1, 0.3 g, 1 mmol, P,P-diphenyl-P-(4-tolylamino)-phosphane (0.44 g, 1.5 mmol, and KHMDS (0.5 M soln in toluene, 0.4 mL, 0.2 mmol) in anhyd toluene (20 mL) was refluxed for 24 h under a nitrogen atmosphere. Then, the solvent was removed under reduced pressure, and the residue was purified by chromatography on deactivated silica gel (5% Et3N in hexane) with EtOAc-hexane 1:1 (v/v) and then EtOAc to yield 6a as orange prisms (from CH2Cl2-Et2O, mp 153-155°C. IR (Nujol, 1505, 1439, 1331, 1181, 1119, 722, 706, 695 cm-1. 1H NMR (400 MHz, CDCl3, δ, 2.29 (s, 3 H, CH3, 6.82-6.86 (m, 6 H, HAr and Ph, 6.93-6.99 (m, 3 H, HAr and Ph, 7.17-7.26 (m, 4 H, Ph2, 7.29-7.45 m, 12 H, Ph2
    • 2 (593.20): C, 78.91; H, 5.60; N, 2.36. Found: C, 79.04; H, 5.46; N, 2.26.
  • 28
    • 58149335975 scopus 로고    scopus 로고
    • Representative Experimental Procedure and Spectral Data for Compounds 8 A solution of 6a (0.78 g, 1.32 mmol) and 4-methoxythiophenol (0.21 g, 1.5 mmol) in anhyd toluene (20 mL) was refluxed for 12 h under a nitrogen atmosphere. Then, the solvent was removed under reduced pressure, and the residue was purified by chromatography on deactivated silica gel (5% Et 3N in hexane) with EtOAc-hexane 1:1 (v/v) and then EtOAc, Z)-P,P-Diphenyl-P-[2-phenyl- 1-(4-methylphenylthio)]ethenylphosphane Oxide (Z-8b) R f, 0.7 (EtOAc, white prisms (from CH2Cl 2-Et2O, mp 126-127°C. IR (Nujol, 1589, 1493, 1434, 1298, 1246, 1201, 723, 694 cm-1. 1H NMR (400 MHz, CDCl3, δ, 3.66 (s, 3 H, OCH3, 6.45 (d, 2 H, 3JHH, 8.9 Hz, HAr, 6.72 d, 2 H, 3JHH
    • 2PS (442.51): C, 73.28; H, 5.24. Found: C, 73.16; H, 5.32.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.