SUPPORTING INFORMATION

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Φιλόθεος Αντωνόπουλος
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1 SUPPRTING INFRMATIN Dihydroxylation of lefins Catalyzed by Zeolite-Confined smium Nanoclusters: A Novel, Effective, Reusable and Eco-Friendly Method for Preparation of 1,2-cis-Diols Önder Metin,*,a Nurdan Alcan Alp, a Serdar Akbayrak, b Abdullah Biçer, a Mehmet Serdar Gültekin,*,a Saim Özkar, b Uğur Bozkaya a a Department of Chemistry, Faculty of Science, Ataturk University, Erzurum, Turkey b Department of Chemistry, Middle East Technical University, Ankara, Turkey ometin@atauni.edu.tr; gultekin@atauni.edu.tr Figure S1. A representativee HRTEM image of zeolite-confined osmium(0) nanoclusters S1

2 Geometry optimizations for theoretical molecular volume computations are carried out using Gaussian 03 program package. Benzoil-cyclohexene ptimized geometry at B3LYP/6-31G(d) level Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z E = a.u., ZPVE = (Kcal/Mol) S2

3 Acetyl-cyclohexen ptimized geometry at B3LYP/6-31G(d) level Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z E = a.u., ZPVE = (Kcal/Mol) Cis-diphenyl-eten ptimized geometry at B3LYP/6-31G(d) level Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z E = a.u., ZPVE = (Kcal/Mol) S3

4 Trans-diphenyl-eten ptimized geometry at B3LYP/6-31G(d) level Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z E = a.u., ZPVE = (Kcal/Mol) Diacetyl-cyclohexen ptimized geometry at B3LYP/6-31G(d) level Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z E = a.u., ZPVE = (Kcal/Mol) S4

5 1 H-NMR and 13 C-NMR spectra and spectral data for cis-diols Ph 1b H 1 H -NMR (200 MHz, CDCl 3, ppm): δ= (5 H, m), 4.75 (1 H,dd, J 8.2, 3.65), 3.63 (1 H, dd, J 11.01, 3.65,), 3.54 (1 H, dd, J 11.01, 8..0). S5

6 H Ph 1b 13 C-NMR (50 MHz, CDCl 3, ppm): δ= 142.5, 130.5, 129.9, 128.1, 76.7, S6

7 Ph H 2b Ph 1 H -NMR (200 MHz, CDCl 3, ppm): δ= (10 H, m), 4.71 (2H, br s) S7

8 Ph H 2b Ph 13 C-NMR (100 MHz, CDCl 3, ppm): δ= 141.9, 130.1, 129.9, 128.9, S8

9 Ph H 3b Ph 1 H -NMR (400 MHz, CDCl 3, ppm): δ= (10H, m), 4.83 (2H, brs), (2H, 2.20 brs) S9

10 Ph H 3b Ph 13 C-NMR (100 MHz, CDCl 3, ppm): δ= 140.0, 128,5, 128.3, 127,3, S10

11 4b 1 H -NMR (400 MHz, CDCl 3, ppm): δ= 3,9 (2H, m), 1.87 (2H, m), 1.58 (2H, m), 1.42 (2H, m). S11

12 4b 13 C-NMR (100 MHz, CDCl 3, ppm): δ= 77.5, 30.9, S12

13 5b 1 H -NMR (400 MHz, CDCl 3, ppm): δ= 3.76 (2H, m), 2.06 (2H, br s, 2H), ( 8H, m) S13

14 5b 13 C-NMR (100 MHz, CDCl 3, ppm): δ= 70.8, 30.1, S14

15 6b 1 H -NMR (400 MHz, CDCl 3, ppm): δ= 3.80 (2H, d, J=8.8 Hz) ), 3.50 (2H, br s, 2H), (10H, m). S15

16 6b 13 C-NMR (100 MHz, CDCl 3, ppm): δ= 74.0, 31.1, 28.0, S16

17 7b 1 H -NMR (400 MHz, CDCl 3, ppm): δ=3.89 (2H, d, J=9.1Hz), 2.2 (2H, br s, 2H), 1.89 (4H, m) ), (8H, m). S17

18 7b 13 C-NMR (100 MHz, CDCl 3, ppm): δ= 73.1, 30.1, 26.2, 23.8 S18

19 8b 1 H -NMR (400 MHz, CDCl 3, ppm): δ=4.43 (1H, t, m), 4.12 (1H, m), 2.47 (2H, m), (2H, m). S19

20 13 C-NMR (100 MHz, CDCl 3, ppm): δ=213.1, 78.8, 69.9, 30.7, b S20

21 9b 1 H -NMR (400 MHz, CDCl 3, ppm): δ=4.40 (1H, dd, J=2.2, 3.5, Hz), 4.14 (1H, m), 2.56 (1H, m) ), 2.38 (1H, m), 2.16 (2H, m), 1.85 (2H, m). S21

22 9b 13 C-NMR (100 MHz, CDCl 3, ppm): δ= 210.2, 77.5, 72.8, 39.2, 28.9, S22

23 Ac 10b 1 H -NMR (400 MHz, CDCl 3, ppm): δ=4.93 (1H, m), 4..00, (1H, m), 3.55 (1H, m), 3.59 (1H, H brs), 3.33 (1H, H brs), (6H, m), 2.03 (3H, s). S23

24 Ac 10b 13 C-NMR (100 MHz, CDCl 3, ppm): δ= 172.0, 74.2, 74.0, 70.1, 30.1, 29.2, 21.6, S24

25 Ac Ac 11b 1 H -NMR (400 MHz, CDCl 3, ppm): δ=5.05 (2H, m), (2H, m), 2.65 (2H, H brs), 1.95 (2(H, m), 1.70 )2H, m), 2.10 (6H, s). S25

26 Ac Ac 11b 13 C-NMR (100 MHz, CDCl 3, ppm): δ=171.1, 72.8, 71.5, 29.9, 23.9, S26

27 Ph 1 H -NMR (400 MHz, CDCl 3, ppm): δ= 8.00 (2H, m aryl), 7.49 (1H, m aryl), 7.38 (2H, m aryl), 5.22 (2H, m), 4.07 (1H,m), 3.72 (1H, m), (6H, m). 12b S27

28 Ph 13 C-NMR (100 MHz, CDCl 3, ppm): δ= 167.1, 133.3, 130.4, 129.9, 128.7, 74.8, 73.9, 70.1, 29.9, 28.9, b S28

29 1 H-NMR spectra of the products obtained by catalytic dihydroxylation of olefins at different temperatures Zeolite-s 0 / H o, 24 h H (CH 2 ) 6 H + H H S29

30 Zeolite-s 0 / H o, 24 h H (CH 2 ) 6 H + H H S30

31 Zeolite-s 0 / H o, 24 h H (CH 2 ) 3 H + H H S31

32 H Zeolite-s 0 / H o, 24 h H + H S32

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