Chloroformyloxylation of Olefins. Generation of Positive Chlorine Ion by the N, N-Dimethylformamide / Hydrogen Chloride / Potassium Monoperoxysulfate System

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• Spectroscopic Data of Products
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• 1-Chloro-2-(formyloxy)cyclohexane (Entry 1): 1H NMR (CDCl3) δ 1.15–2.45 (m, 8H), 3.80–4.10 (m, 1H), 4.85–5.05 (m, 1H), 8.15 (s, 1H); 13C NMR (CDCl3) δ 22.76, 24.02, 30.38, 34.34, 59.95, 75.33, 159.76; MS (70 eV) m/z (rel. intensity) 57 (100), 80 (100), 81 (100), 84 (100), 86 (87), 134 (2), 163 (M++1, 3)
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• 1-Chloro-2-(formyloxy)cycloheptane (Entry 2): 1H NMR (CDCl3) δ 1.40–2.35 (m, 10H), 4. 00–4.20 (m, 1H), 5.05–5.20 (m, 1H), 8.10 (s, 1H); MS (70 eV) m/z (rel. intensity) 57 (69), 68 (65), 84 (100), 86 (100), 95 (100), 147 (1), 177 (M++1, 1)
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• 1-Chloro-2-(formyloxy)cyclopentane (Entry 3): 1H NMR (CDCl3) δ 1.60–2.40 (m, 6H), 4. 15–4.30 (m, 1H), 5.20–5.35 (m, 1H), 8.02 (s, 1H); MS (70 eV) m/z (rel. intensity) 66 (53), 67 (100), 102 (7i), 104 (30), 120 (M+-CHO+1, 47), 122 (13)
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• 3-Chloro-4-(formyloxy)tetrahydrofuran (Entry 4): 1H NMR (CDCl3) δ 3.85–4.40 (m, 4H), 4. 40–4.55 (m, 1H), 5.43 (m, 1H), 8.05 (s, 1H); MS (70 eV) m/z (rel. intensity) 69 (11), 84 (100), 86 (69), 88 (13), 121 (M+-CHO, 1)
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• 1-Chloro-2-(formyloxy)hexane and 2-Chloro-1-(formyloxy)-hexane (Entry 5): 1H NMR (CDCl3) δ 0.80–1.00 (m, 3H), 1.20–1.55 (m, 4H), 1.60–1.85 (m, 2H), 3.60–3.70 (m, 1.4H), 4.05–4.15 (m, 0.3H), 4.30–4.38 (m, 0.6H), 5.10–5.25 (m, 0.7H); MS (70 eV) m/z (rel. intensity) 69 (100), 83 (77), 84 (100), 86 (100), 135 (1), 165 (M++1, 1)
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