2013
DOI: 10.1016/j.jorganchem.2012.09.018
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Solution-state 15N NMR and solid-state single-crystal XRD study of heterosubstituted diazaboroles and borinines prepared via an effective and simple microwave-assisted solvent-free synthesis

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Cited by 14 publications
(3 citation statements)
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“…Following the general procedure B, 2g was obtained from p-anisidine (151.9 mg, 1.0 mmol) and 1,8diaminonaphtalene (158.2 mg, 1.0 mmol) as a brown solid (113.9 mg, 41.5%) after preparative TLC on silica, eluting with pentane/ (85:15). The 1 H and 13 C data were consistent with those reported in the literature: 34 General Procedure C for Biaryl Compounds Synthesis. To a solution of aniline (93.1 mg, 1.0 mmol, 1.0 equiv) in HCl (2.1 M in water, 1.2 mL, 2.5 mmol, 2.5 equiv) at 0 °C was added a solution of NaNO 2 (2.4 M in water, 0.5 mL, 1.2 mmol, 1.2 equiv) dropwise, and the reaction mixture was stirred for 15 min at 0 °C.…”
Section: ■ Experimental Sectionsupporting
confidence: 88%
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“…Following the general procedure B, 2g was obtained from p-anisidine (151.9 mg, 1.0 mmol) and 1,8diaminonaphtalene (158.2 mg, 1.0 mmol) as a brown solid (113.9 mg, 41.5%) after preparative TLC on silica, eluting with pentane/ (85:15). The 1 H and 13 C data were consistent with those reported in the literature: 34 General Procedure C for Biaryl Compounds Synthesis. To a solution of aniline (93.1 mg, 1.0 mmol, 1.0 equiv) in HCl (2.1 M in water, 1.2 mL, 2.5 mmol, 2.5 equiv) at 0 °C was added a solution of NaNO 2 (2.4 M in water, 0.5 mL, 1.2 mmol, 1.2 equiv) dropwise, and the reaction mixture was stirred for 15 min at 0 °C.…”
Section: ■ Experimental Sectionsupporting
confidence: 88%
“…Following the general procedure B, 2g was obtained from p -anisidine (151.9 mg, 1.0 mmol) and 1,8-diaminonaphtalene (158.2 mg, 1.0 mmol) as a brown solid (113.9 mg, 41.5%) after preparative TLC on silica, eluting with pentane/EtOAc (85:15). The 1 H and 13 C data were consistent with those reported in the literature: mp 128–131 °C; ν max (film)/cm –1 3408, 1723, 1595, 1492, 1406, 1224, 1179, 1085, 1028, 818, 760; 1 H NMR (400.0 MHz; CDCl 3 ) δ H = 7.57 (d, J = 8.1 Hz, 2H, ArH), 7.15 (t, J = 7.4 Hz, 2H, ArH), 7.06 (d, J = 8.1 Hz, 2H, ArH), 6.97 (d, J = 7.4 Hz, 2H, ArH), 6.40 (d, J = 7.4 Hz, 2H, ArH), 5.98 (br s, 2H, 2 × NH), 3.84 (s, 3H, CH 3 ); 13 C NMR (100.6 MHz; CDCl 3 ) δ C = 161.5 (ArC), 141.4 (ArC), 136.5 (ArC), 133.2 (2 × ArCH), 127.8 (2 × ArCH), 119.8 (2 × ArC), 117.8 (2 × ArCH), 114.0 (2 × ArCH), 106.1 (2 × ArCH), 55.3 (CH 3 ); 11 B NMR (128.4 MHz; CDCl 3 ) δ B = 29.3 (br).…”
Section: Experimental Sectionsupporting
confidence: 87%
“…Alternatively, three-coordinate boron compounds functionalized with 1,3,2-benzodiazaborole units are greatly stabilised by electron back-donation from the two nitrogen atoms to the empty boron p z -orbital (Fig. 2, compound 6 ) [1314]. …”
Section: Introductionmentioning
confidence: 99%