S([O-])([O-])(=O)=O.[Na+].[Na+].[OH-].[K+].[CH2:10]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21](=[N:28][NH2:29])[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:17][CH:16]=1)[CH:11]=[CH2:12]>C(O)C.[Hg]=O>[CH2:10]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21](=[N+:28]=[N-:29])[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:17][CH:16]=1)[CH:11]=[CH2:12]To a mixture of mercury (II) oxide (3.1 g, 14 mmol), sodium sulphate (2.4 g, 16 mmol) and sat potassium hydroxide in ethanol (3 ml) was added a solution of 10 (3.2 g, 12 mmol) in dry TIM (20 ml). The mixture was stirred in the dark for 2 h. then filtered through a celite pad. Concentration of the filtrate in vacuo yielded 11 (3.1 g, 100%) as a dark red oil; δH (CDCl3) 3.90-3.94 (m, 2H, OCH2CH═CH2), 4.38 (s, 2H, ArCH2O), 5.05-5.26 (m, 2H, OCH2CH═CH2), 5.74-5.94 (m, 1H, OCH2CH═CH2), 7.12-7.36 (m, 9H, Ar—H) ppm; δC 71.0, 71.6 (OCH2CH═CH2, ArCH2O), 117.0 (OCH2CH═CH2), 124.9, 125.0, 125.4, 128.5, 129.0 (Ar—C), 129.8, 130.1 (1-, 1′-C), 134.5 (OCH2CH═CH2), 135.6 (4-C) ppm; νmax (thin film) 3029, 2855, 2038, 1596, 1512, 1494, 1085 cm−1; m/z (Fr) 264 ([M]+, 70%), 252 (100%), 196 (35%); found (Fr) 264.1250, C17H16N2O requires 264.1263.
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