Supporting Information. Fe(II)/Fe(III)-catalyzed Intramolecular Didehydro-Diels-Alder Reaction. of Styrene-ynes
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1 Supporting Information Fe(II)/Fe(III)-catalyzed Intramolecular Didehydro-Diels-Alder Reaction of Styrene-ynes Hyeon Jin Mun, Eun Young Seong, Kwang-Hyun Ahn*, and Eun Joo Kang* Department of Applied Chemistry, Kyung Hee University, Yongin 17104, Korea * Table of Contents I. Supplementary Computational Information S2 II. Spectroscopic Data S11 S1
2 I. Supplementary Computational Information Table S1. Cartesian Atomic Coordinates for the Geometry Optimized Structure of A in Figure 1 [B3LYP/6-31G(d)] atom x/å y/ Å z/ Å C C C C C H H H H C C N C H H C H C H C C C C H C H C H H H C H H C H S S2
3 O O C H H H Table S2. Cartesian Atomic Coordinates for the Geometry Optimized Structure of B in Figure 1 [B3LYP/6-31G(d)] atom x/å y/ Å z/ Å C C C C C C H H H H H C C N C H H C H C H C C C C H C H C H S3
4 H H S O O C H H C H H H Table S3. Cartesian Atomic Coordinates for the Geometry Optimized Structure of TS in Figure 1 [B3LYP/6-31G(d)] atom x/å y/ Å z/ Å C C C C C C H H H H H C C N C H H C H C H C C C S4
5 C H C H C H H H S O O C H H C H H H Table S4. Cartesian Atomic Coordinates for the Geometry Optimized Structure of A-FeCl2 in Figure 1 (B3LYP/gen) atom x/å y/ Å z/ Å C C C C C H H H H C C N C H H C H C S5
6 H C C C C H C H C H H H C H H Fe C H Cl Cl S O O C H H H Table S5. Cartesian Atomic Coordinates for the Geometry Optimized Structure of B-FeCl2 in Figure 1 (B3LYP/gen) atom x/å y/ Å z/ Å C C C C C H H H H S6
7 C C N C H H C H C H C C C C H C H C H H H C H H Fe C H Cl Cl S O O C H H H Table S6. Cartesian Atomic Coordinates for the Geometry Optimized Structure of TS-FeCl2 in Figure 1 (B3LYP/gen) atom x/å y/ Å z/ Å S7
8 C C C C C H H H H C C N C H H C H C H C C C C H C H C H H H C H H Fe C H Cl Cl S O O S8
9 C H H H Table S7. Cartesian Atomic Coordinates for the Geometry Optimized Structure of B-FeCl3 in Figure 2 (B3LYP/gen) atom x/å y/ Å z/ Å C C C C C H H H H C C N C H H C H C H C C C C H C H C H H H C H S9
10 H Fe C H Cl Cl S O O C H H H Cl S10
11 II. Spectroscopic Data 4-p-tolyl-2-tosyl-2,3-dihydro-1H-benzo[f]isoindole 2b b S11
12 S12
13 H H 2a 2b H D D D D D D D D D D 2a(D) 2b(D) S13
14 9-m-tolyl-2-tosyl-2,3,3a,4-tetrahydro-1H-benzo[f]isoindole 3a + 4-m-tolyl-2-tosyl-2,3-dihydro-1H-benzo[f]isoindole 3b (sample of a 4:96 mix after recrystallization) a 3b S14
15 S15
16 4-(4-methoxyphenyl)-2-tosyl-2,3-dihydro-1H-benzo[f]isoindole 4b OMe 4b S16
17 S17
18 9-(2-methoxyphenyl)-2-tosyl-2,3,3a,4-tetrahydro-1H-benzo[f]isoindole 5a + 4-(2-methoxyphenyl)-2-tosyl-2,3-dihydro-1H-benzo[f]isoindole 5b (15:85) OMe OMe 5a 5b S18
19 S19
20 4-(4-bromophenyl)-2-tosyl-2,3-dihydro-1H-benzo[f]isoindole 6b Br 6b S20
21 S21
22 9-(thiophen-2-yl)-2-tosyl-2,3,3a,4-tetrahydro-1H-benzo[f]isoindole 7a + 4-(thiophen-2-yl)-2-tosyl-2,3-dihydro-1H-benzo[f]isoindole 7b (13:87) N 8b S22
23 S23
24 4-(pyridin-2-yl)-2-tosyl-2,3-dihydro-1H-benzo[f]isoindole 8b S S 7a 7b S24
25 S25
26 9-(naphthalen-1-yl)-2-tosyl-2,3,3a,4-tetrahydro-1H-benzo[f]isoindole 9a + 4-(naphthalen-1-yl)-2-tosyl-2,3-dihydro-1H-benzo[f]isoindole 9b (10:90) a 9b S26
27 S27
28 6-methyl-4-p-tolyl-2-tosyl-2,3-dihydro-1H-benzo[f]isoindole 10b b S28
29 S29
30 8-methoxy-4-p-tolyl-2-tosyl-2,3-dihydro-1H-benzo[f]isoindole 11b b OMe S30
31 S31
32 6-bromo-4-p-tolyl-2-tosyl-2,3-dihydro-1H-benzo[f]isoindole 12b Br 12b S32
33 S33
34 4-p-tolyl-6-tosyl-6,7,7a,8-tetrahydro-5H-thieno[3,2-f]isoindole 13a + 4-p-tolyl-6-tosyl-6,7-dihydro-5H-thieno[3,2-f]isoindole 13b (11:89) a S 13b S S34
35 S35
36 7-p-tolyl-9-tosyl-9,10,10a,11-tetrahydro-8H-naphtho[2,1-f]isoindole 15a + 7-p-tolyl-9-tosyl-9,10-dihydro-8H-naphtho[2,1-f]isoindole 15b (10:90) a 15b S36
37 S37
38 11-p-tolyl-9-tosyl-9,10-dihydro-8H-naphtho[1,2-f]isoindole 16b b S38
39 S39
40 5-methyl-4-p-tolyl-2-tosyl-2,3-dihydro-1H-benzo[f]isoindole 17b + 7-methyl-4-p-tolyl-2-tosyl-2,3-dihydro-1H-benzo[f]isoindole 17b (66:34) b 17b' S40
41 S41
42 4-p-tolyl-1,3-dihydronaphtho[2,3-c]furan 18b O 18b S42
43 S43
44 diethyl 4-p-tolyl-1H-cyclopenta[b]naphthalene-2,2(3H)-dicarboxylate 19b + diethyl 2-cinnamyl- 2-(3-p-tolylprop-2-ynyl)malonate (30:70) EtO 2 C EtO 2 C EtO 2 C EtO 2 C 19b S44
45 S45
46 2-tosyl-4-(trimethylsilyl)-2,3-dihydro-1H-benzo[f]isoindole 21b TMS 21b S46
47 S47
48 4-methyl-2-tosyl-2,3-dihydro-1H-benzo[f]isoindole 23b b S48
49 S49
50 5-methyl-4-p-tolyl-2-tosylisoindoline 27b b S50
51 S51
52 5-methyl-2-tosyl-4-(trimethylsilyl)isoindoline 29b TMS 29b S52
53 S53
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