SUPPORTING INFORMATION

Transcription

1 SUPPORTING INFORMATION Difunctionalization of Styrenes with Perfluoroalkyl and tert- Butylperoxy Radicals: Room Temperature Synthesis of (1- (tert-butylperoxy)-2-perfluoroalkyl)ethylbenzene Erbo Shi, Jiajun Liu, Chunmei Liu, Ying Shao, Hanghang Wang, Yuanzheng Lv, Meishan Ji, Xiaoguang Bao* and Xiaobing Wan* Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou , P. R. China Key Laboratory of Advanced Catalytic Materials and Technology, Advanced Catalysis and Green Manufacturing Collaborative Innovation Center, Changzhou University Changzhou , P. R. China Table of Contents Trapping of Radicals Spectroscopic Data For Products Cartesian Coordinates and Energies

2 Trapping of Radicals Scheme S1. Trapping of Radicals by TEMPO a a TEMPO was added after the standard system being stirred for 5 minutes, the reaction was stopped after another 10 minutes. MSD1 SPC, time= of Z:\WXB\12-14\LCM D ES-API, Pos, Scan, Frag: Max: m/z 2

3 376.0 a TEMPO was added after the standard system being stirred for 5 minutes, the reaction was stopped after another 10 minutes. MSD1 SPC, time= of Z:\WXB\12-14\LCM D ES-API, Pos, Scan, Frag: Max: m/z 3

4 3a Spectroscopic Data for Products 4

5 3a 5

6 3a 6

7 3b 7

8 3b 8

9 3b 9

10 3c 10

11 3c 11

12 3c 12

13 3d 13

14 3d 14

15 3d 15

16 3e 16

17 3e 17

18 3e 18

19 3f 19

20 3f 20

21 3f 21

22 3g 22

23 3g 23

24 3g 24

25 3h 25

26 3h 26

27 3h 27

28 3i 28

29 3i 29

30 3i 30

31 3j 31

32 3j 32

33 3j 33

34 3k 34

35 3k 35

36 3k 36

37 3l 37

38 3l 38

39 3l 39

40 3m 40

41 3m 41

42 42 3m

43 4a 43

44 4a 44

45 4a 45

46 4b 46

47 4b 47

48 4b 48

49 4c 49

50 4c 50

51 4c 51

52 4d 52

53 4d 53

54 4d 54

55 4e 55

56 4e 56

57 4e 57

58 4f 58

59 4f 59

60 4f 60

61 4g 61

62 4g 62

63 63 4g

64 7 64

65 7 65

66 7 66

67 8 67

68 8 68

69 8 69

70 9 70

71 9 71

72 9 72

73 10 73

74 7410

75 75 10

76 Cartesian Coordinates and Energies TS1 Standard orientation: Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z Zero-point correction= (Hartree/Particle) Thermal correction to Energy= Thermal correction to Enthalpy= Thermal correction to Gibbs Free Energy= Sum of electronic and zero-point Energies= Sum of electronic and thermal Energies= Sum of electronic and thermal Enthalpies= Sum of electronic and thermal Free Energies= M06-2X/ G(d,p) /PCM // M06-2X/6-31+G(d,p) energy= TS2 Standard orientation: Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z

77 Zero-point correction= (Hartree/Particle) Thermal correction to Energy= Thermal correction to Enthalpy= Thermal correction to Gibbs Free Energy= Sum of electronic and zero-point Energies= Sum of electronic and thermal Energies= Sum of electronic and thermal Enthalpies= Sum of electronic and thermal Free Energies= M06-2X/ G(d,p) /PCM // M06-2X/6-31+G(d,p) energy= TS3 Standard orientation: Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z Zero-point correction= (Hartree/Particle) Thermal correction to Energy= Thermal correction to Enthalpy= Thermal correction to Gibbs Free Energy= Sum of electronic and zero-point Energies= Sum of electronic and thermal Energies= Sum of electronic and thermal Enthalpies=

78 Sum of electronic and thermal Free Energies= M06-2X/ G(d,p) /PCM // M06-2X/6-31+G(d,p) energy= Styrene Standard orientation: Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z Zero-point correction= (Hartree/Particle) Thermal correction to Energy= Thermal correction to Enthalpy= Thermal correction to Gibbs Free Energy= Sum of electronic and zero-point Energies= Sum of electronic and thermal Energies= Sum of electronic and thermal Enthalpies= Sum of electronic and thermal Free Energies= M06-2X/ G(d,p) /PCM // M06-2X/6-31+G(d,p) energy= A Standard orientation: Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z Zero-point correction= (Hartree/Particle) Thermal correction to Energy=

79 Thermal correction to Enthalpy= Thermal correction to Gibbs Free Energy= Sum of electronic and zero-point Energies= Sum of electronic and thermal Energies= Sum of electronic and thermal Enthalpies= Sum of electronic and thermal Free Energies= M06-2X/ G(d,p) /PCM // M06-2X/6-31+G(d,p) energy= B Standard orientation: Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z Zero-point correction= (Hartree/Particle) Thermal correction to Energy= Thermal correction to Enthalpy= Thermal correction to Gibbs Free Energy= Sum of electronic and zero-point Energies= Sum of electronic and thermal Energies= Sum of electronic and thermal Enthalpies= Sum of electronic and thermal Free Energies= M06-2X/ G(d,p) /PCM // M06-2X/6-31+G(d,p) energy= C Standard orientation: Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z

80 Zero-point correction= (Hartree/Particle) Thermal correction to Energy= Thermal correction to Enthalpy= Thermal correction to Gibbs Free Energy= Sum of electronic and zero-point Energies= Sum of electronic and thermal Energies= Sum of electronic and thermal Enthalpies= Sum of electronic and thermal Free Energies= M06-2X/ G(d,p) /PCM // M06-2X/6-31+G(d,p) energy= Rf Standard orientation: Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z Zero-point correction= (Hartree/Particle) Thermal correction to Energy= Thermal correction to Enthalpy= Thermal correction to Gibbs Free Energy= Sum of electronic and zero-point Energies= Sum of electronic and thermal Energies= Sum of electronic and thermal Enthalpies= Sum of electronic and thermal Free Energies= M06-2X/ G(d,p) /PCM // M06-2X/6-31+G(d,p) energy= t-buoo Standard orientation: Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z

81 Zero-point correction= (Hartree/Particle) Thermal correction to Energy= Thermal correction to Enthalpy= Thermal correction to Gibbs Free Energy= Sum of electronic and zero-point Energies= Sum of electronic and thermal Energies= Sum of electronic and thermal Enthalpies= Sum of electronic and thermal Free Energies= M06-2X/ G(d,p) /PCM // M06-2X/6-31+G(d,p) energy= t-buo Standard orientation: Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z Zero-point correction= (Hartree/Particle) Thermal correction to Energy= Thermal correction to Enthalpy= Thermal correction to Gibbs Free Energy= Sum of electronic and zero-point Energies= Sum of electronic and thermal Energies= Sum of electronic and thermal Enthalpies= Sum of electronic and thermal Free Energies= M06-2X/ G(d,p) /PCM // M06-2X/6-31+G(d,p) energy=