Iron(III) Tosylate
2615
1
1,3-Diphenylacetone diethyl acetal: A colorless oil; H NMR d: 7.37–7.16
(m, 10 H), 3.59–3.51 (m, 4 H), 3.02 (s, 4 H), 1.23 (dd, J ¼ 6.9, 7.0 Hz,
3 H), 1.22 (dd, J ¼ 7.0 Hz, 3 H); 13C NMR d: 137.2, 130.4, 127.7, 126.0,
103.0, 55.3, 40.1, 15.0; MS m=z (%): 239 (Mþ -OEt, 12), 193 (80), 91
(100).
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2-Methylcyclohexanone diethyl acetal: A colorless oil; H NMR d: 3.45–
3.25 (m, 4 H), 2.17–2.03 (m, 1 H), 1.94–1.82 (m, 1 H), 1.77–1.68 (m,
1 H), 1.55–1.31 (m, 6 H), 1.11–1.03 (m, 6 H), 0.96 (d, J ¼ 7.2 Hz, 3 H);
13C NMR d: 101.5, 54.3, 53.8, 34.3, 29.2, 28.2, 22.8, 20.0, 15.2, 15.1,
13.9; MS m=z (%): 186 (Mþ, 39), 141 (Mþ -OEt, 80), 129 (100).
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Cycloheptanone diethyl acetal: A colorless oil; H NMR d: 3.49 (ddd,
J ¼ 7.0, 7.0, 7.0 Hz, 4 H), 1.89–1.80 (m, 4 H), 1.59–1.43 (m, 8 H), 1.13
(dd, J ¼ 7.0, 7.0 Hz, 6 H); 13C NMR d: 103.8, 54.8, 37.0, 29.0, 21.8,
15.3; MS m=z (%): 186 (Mþ, 8), 141 (Mþ -OEt, 97), 129 (100).
Cyclooctanone diethyl acetal: A colorless oil; 1H NMR d: 3.39 (ddd,
J ¼ 7.0, 7.0, 7.0 Hz, 2 H), 3.38 (ddd, J ¼ 7.0, 7.0, 7.0 Hz, 2 H), 1.88–
1.80 (m, 4 H), 1.62–1.42 (m, 10 H), 1.13 (dd, J ¼ 7.0, 7.0 Hz, 3 H), 1.12
(dd, J ¼ 7.0, 7.0 Hz, 3 H); 13C NMR d: 103.3, 54.73, 31.3, 28.1, 24.4,
21.4, 15.3; MS m=z (%): 200 (Mþ , 20), 155 (Mþ -OEt, 83), 129 (100).
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Cyclododecanone diethyl acetal: A colorless oil; H NMR d: 3.41 (ddd,
J ¼ 7.0, 7.0, 7.0 Hz, 4 H), 1.77–1.68 (m, 4 H), 1.40–1.30 (m, 18 H), 1.15
(dd, J ¼ 7.0, 7.0 Hz, 6 H); 13C NMR d: 103.4, 54.8, 30.3, 26.2, 26.0,
22.3, 21.9, 19.4, 15.2; MS m=z (%): 256 (Mþ , 7), 211, Mþ - OEt, 76),
129 (100).
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Chloroacetone diethyl acetal: A colorless oil; H NMR d: 3.34 (s, 2H),
3.35–3.22 (m, 4 H), 1.33 (s, 3 H), 1.02 (dd, J ¼ 7.0, 7.0 Hz, 6 H); 13C
NMR d: 99.7, 55.8, 46.4, 20.7, 14.9; MS m=z (%): 316 (Mþ , 5), 271
(Mþ - OMe, 100).
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d,l-Camphor diethyl acetal: A colorless oil; H NMR d: 3.63–3.50 (m,
1 H), 3.44–3.25 (m, 3 H), 2.23–2.11 (m, 1 H), 1.94–1.82 (m, 1 H), 1.82–
1.74 (m, 1 H), 1.59 (dd, J ¼ 4.7, 4.7 Hz, 1 H), 1.40–1.32 (m, 3 H), 1.08
(dd, J ¼ 7.0, 7.1 Hz, 3 H), 1,07 (dd, J ¼ 7.0, 7.0 Hz, 3 H), 1.07 (s, 3 H),
1.04 (s, 3 H), 0.82 (s, 3 H); 13C NMR d: 108.7, 57.4, 55.1, 53.3, 50.1,
44.8, 42.0, 29.7, 27.7, 21.1, 20.8, 15.7, 15.5, 12.6; MS m=z (%): 226
(Mþ, 22), 211 (8), 181(Mþ -OEt, 25), 95 (100).
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Ethyl acetoacetate diethyl acetal: A colorless oil; H NMR d: 3.94 (ddd,
J ¼ 7.1, 7.1, 7.1 Hz, 2 H), 3.52–3.30 (m, 4 H), 2.70 (s, 2 H), 1.60 (s,
3 H), 1.08 (dd, J ¼ 7.0, 7.1 Hz, 6 H), 0.94 (dd, J ¼ 7.1, 7.1 Hz, 3 H); 13C
NMR dv: 169.2, 99.8, 60.0, 56.0, 43.4, 23.1, 15.4, 14.1; MS m=z (%):
159 (Mþ -OEt, 100).
Ethyl (2E)-3-ethoxy-2-butenoate:
A
light yellow oil; 1H NMRd:
5.05 (s,1 H), 4.13 (ddd, J ¼ 7.1, 7.1, 7.1 Hz, 2 H), 3.21 (ddd, J ¼ 7.0,
7.0, 7.0 Hz, 2 H), 2.43 (s, 3 H), 1.08 (dd, J ¼ 7.1, 7.1 Hz, 3 H),