Heavier chalcogenone complexes of bismuth(iii)trihalides: Potential catalysts for acylative cleavage of cyclic ethers. Supporting Information
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1 Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2015 Heavier chalcogenone complexes of bismuth(iii)trihalides: Potential catalysts for acylative cleavage of cyclic ethers Katam Srinivas, Paladugu Suresh, Chatla aga Babu, Arruri Sathyanarayana and Ganesan Prabusankar* Department of Chemistry, Indian Institute of Technology Hyderabad, DF Campus, Yeddumailaram, AP, IDIA Fax: ; Tel: ; Ph Me S S Me Bi Williams et al. (1989) S R' R' R' S [1:2] H B S Bi S R' S Ph Bi Shu et al. (2004) [1:3] Ph R' S R' R Bi S R' Supporting Information H X' R' X' B R' X' R S R S S R R Bi X S S R S R X' B X' R' R' X' H R = Me, X' = C, R' = H, X = Tp 2 a R = Me, X' =, R' = Me, X = R = Et, X' =, R' = Me, X = 3 R = Ph, R' = Me, X' =, X = 3 Reglinski et al. (1999) Bailey et al. (2001) Marchio et al. (2003) Marchio et al. (2004) [1:6] R = R' = Et R = Me, R' = ipr R = Me, R' = Pr Battaglia et al. (1983) Williams et al. (2007) [1:2] Me S HB Bi S Me S Me Me S Me S Bi S BH Me nbu nbu Se I nbu Singh et al. (2013) [1:1] I Bi I I nbu Se Bi I I I I Bi nbu I I Bi Se Reglinski et al. (1999) [1:3] I nbu I Se nbu nbu Scheme S1. The structurally characterized monomeric, dimeric and tetrameric bismuth complexes of imazolyl heavier chalcogenone. Page 1 of 27
2 Transmittance [%] Wavenumber cm Figure S1. FT-IR (neat) spectrum of IPr=Te (5) at RT. Figure S2. 1 H MR spectrum of IPr=Te (5) in CD 3 at RT. Page 2 of 27
3 Figure S3. 13 C MR spectrum of IPr=Te (5) in CD 3 at RT Transmittance [%] Wavenumber cm Figure S4. FT-IR (neat) spectrum of [(IPr=Te)Bi 3 ] (10) at RT. Page 3 of 27
4 Transmittance [%] Wavenumber cm Figure S5. FT-IR (neat) spectrum of [(IPr=Te)BiBr 3 ] (11) at RT Transmittance [%] Wavenumber cm Figure S6. FT-IR (neat) spectrum of [(IPr=S)Bi 3 ].CH 3 (6) at RT. C:\Program Files (x86)\pus_65\meas\.2228 GP-KS-L-2-19 SLID 21/12/2013 Page 1/1 Page 4 of 27
5 Figure S7. 1 H MR spectrum of [(IPr=S)Bi 3 ].CH 3 (6) in CD 3 at RT. Page 5 of 27
6 Figure S8. 13 C MR spectrum of [(IPr=S)Bi 3 ].CH 3 (6) in CD 3 at RT Transmittance [%] Wavenumber cm Figure S9. FT-IR (neat) spectrum of [(IPr=S)BiBr 3 ].CH 3 (7) at RT. Figure S10. 1 H MR spectrum of [(IPr=S)BiBr 3 ].CH 3 (7) in CD 3 at RT. Page 6 of 27
7 Figure S C MR spectrum of [(IPr=S)BiBr 3 ].CH 3 (7) in CD 3 at RT Transmittance [%] Wavenumber cm Figure S12. FT-IR (neat) spectrum of [(IPr=Se)Bi 3 ].CH 2 2 (8) at RT. Page 7 of 27
8 Figure S13. 1 H MR spectrum of [(IPr=Se)Bi 3 ].CH 2 2 (8) in CD 3 at RT. Page 8 of 27
9 Figure S C MR spectrum of [(IPr=Se)Bi 3 ].CH 2 2 (8) in CD 3 at RT Transmittance [%] Wavenumber cm Figure S15. FT-IR (neat) spectrum of [(IPr=Se)BiBr 3 ].CH 2 2 (9) at RT. Page 9 of 27
10 Figure S16. 1 H MR spectrum of [(IPr=Se)BiBr 3 ].CH 2 2 (9) in CD 3 at RT. Page 10 of 27
11 Figure S C MR spectrum of [(IPr=Se)BiBr 3 ].CH 2 2 (9) in CD 3 at RT Transmittance [%] Wavenumber cm Figure S18. FT-IR (neat) spectrum of [(IMesS)Bi() 2 (μ 2 -)] 2.4CH 3 (12) at RT. Page 11 of 27
12 Figure S19. 1 H MR spectrum of [(IMesS)Bi() 2 (μ 2 -)] 2.4CH 3 (12) in CD 3 at RT. Page 12 of 27
13 Figure S C MR spectrum of [(IMesS)Bi() 2 (μ 2 -)] 2.4CH 3 (12) in CD 3 at RT Transmittance [%] Wavenumber cm Figure S21. FT-IR (neat) spectrum of [(IMesS)Bi(Br) 2 (μ 2 -Br)] 2.2CH 3 (13) at RT. Page 13 of 27
14 Figure S22. 1 H MR spectrum of [(IMesS)Bi(Br) 2 (μ 2 -Br)] 2.2CH 3 (13) in CD 3 at RT. Figure S C MR spectrum of [(IMesS)Bi(Br) 2 (μ 2 -Br)] 2.2CH 3 (13) in CD 3 at RT. Page 14 of 27
15 Transmittance [%] Wavenumber cm Figure S24. FT-IR (neat) spectrum of [(IMesSe)Bi() 2 (μ 2 -)] 2.4CH 2 2 (14) at RT. Figure S25. 1 H MR spectrum of [(IMesSe)Bi() 2 (μ 2 -)] 2.4CH 2 2 (14) in CD 3 at RT. Page 15 of 27
16 Figure S C MR spectrum of [(IMesSe)Bi() 2 (μ 2 -)] 2.4CH 2 2 (14) in CD 3 at RT. Transmittance [%] Wavenumber cm Figure S27. FT-IR (neat) spectrum of [(IMesSe)Bi(Br) 2 (μ 2 -Br)] 2 (15) at RT. Page 16 of 27
17 Figure S28. 1 H MR spectrum of [(IMesSe)Bi(Br) 2 (μ 2 -Br)] 2 (15) in CD 3 at RT. Page 17 of 27
18 Figure S C MR spectrum of [(IMesSe)Bi(Br) 2 (μ 2 -Br)] 2 (15) in CD 3 at RT. Transmittance [%] Wavenumber cm Figure S30. FT-IR (neat) spectrum of [(IMesTe)Bi() 2 (μ 2 -)] 2 (16) at RT. Transmittance [%] Wavenumber cm Figure S31. FT-IR (neat) spectrum of [(IMesTe)Bi(Br) 2 (μ 2 -Br)] 2 (17) at RT. D:\DATA\FTIR DATA\Dr.G.PRABUSAKAR\K.SRIIVAS\IMes=Te-BiBr3.0 IMes=Te-BiBr3 solid 25/05/2014 Page 1/1 Page 18 of 27
19 Figure S32. The solution state UV-vis spectra of 3-5 in DCM at 25 o C (3.8 X 10-2 M). Figure S33. The solid state UV-vis spectra of 3-5. Page 19 of 27
20 Figure S34. The solution state UV-vis spectra of 3a-5a in DCM at 25 o C (3.8 X 10-2 M). Figure S35. The solid state UV-vis spectra of 3a-5a. Page 20 of 27
21 Table S1a. Structural parameters of compounds 3, Empirical formula C 6.75 H S 0.25 C 6.75 H Te 0.25 C 7 H S Bi 0.25 C 14 H 18.5 S 0.5 Br 1.5 Bi C 7 H Bi 0.25Se 0.25 C 28 H 38 BiBr 3 2 2Se Formula weight Temperature (K) Crystal system Monoclinic Monoclinic Monoclinic Triclinic Monoclinic Monoclinic Space group P2 1 /n P2 1 /n P2 1 /c Pī P2 1 /c P2 1 /c a/å (14) (5) (3) (4) (16) (2) b/å (4) (17) (5) (6) (2) (3) c/å (17) (8) (7) (7) (4) (4) α/ (4) β/ (8) (4) (3) (4) (16) (2) γ/ (4) Volume (Å 3 ) (3) (16) (18) (15) (9) (12) Z ρ calc /mg mm Absorption coefficient (µ/mm -1 ) F(000) Reflections collected R int GF on F R 1 (I>2ϭ(I)) wr 2 (I>2ϭ(I)) R 1 values (all data) R 2 values (all data) Page 21 of 27
22 Table S1b. Structural parameters of compounds 4a and a Empirical formula C 21 H 24 2 Se C 46 H 52 Bi S 2 C 46 H 52 Bi 2 Br S 2 C 23H 28Bi 7 2 Se C 42H 48 4 Se 2 Bi 2 Br 6 Formula weight Temperature (K) Crystal system rthorhombic Monoclinic Triclinic Monoclinic Monoclinic Space group Pbcn P2 1 /n Pī P2 1 /c P2 1 /c a/å (9) (8) (5) (6) (2) b/å (3) (9) (6) (4) (4) c/å (5) (7) (7) (6) (4) α/ (5) β/ (5) (4) (3) (2) γ/ (4) Volume (Å 3 ) (14) (3) (16) (19) (10) Z ρ calc /mg mm Absorption coefficient (µ/mm -1 ) F(000) Reflections collected R int GF on F R 1 (I>2ϭ(I)) wr 2 (I>2ϭ(I)) R 1 values (all data) R 2 values (all data) Page 22 of 27
23 Table S2. Selected bond lengths and angles of compounds Bond lengths [Å] Bi(1) E(1) 2.929(2) 2.940(18) 2.971(5) 2.980(8) Bi(1) X(1) 2.578(3) 2.615(8) 2.473(12) 2.620(9) Bi(1) X(2) 2.452(3) 2.731(9) 2.486(13) 2.760(9) Bi(1) X(3) 2.479(2) 2.610(8) 2.594(13) 2.630(10) C(1) E(1) 1.696(10) 1.694(7) 1.861(5) 1.861(8) Bond angles [ o ] (1) C(1) (2) 106.1(8) 105.9(6) 106.1(4) 105.9(6) (1) C(1) E(1) 130.1(7) 125.5(5) 125.3(3) 129.2(5) (2) C(1) E(1) 123.7(7) 128.7(5) 108.5(3) 124.8(5) C(1) E(1) Bi(1) 108.8(3) 114.1(2) (13) 111.5(2) X(1) Bi(1) X(2) 93.08(9) 93.28(3) 90.93(5) 91.21(3) X(1) Bi(1) X(3) 90.27(10) 94.71(3) 89.40(5) 92.86(3) X(2) Bi(1) X(3) 94.70(9) 93.76(3) 94.48(5) 94.19(3) X(1) Bi(1) E(1) 70.47(9) 80.75(4) 75.33(3) 76.53(3) X(2) Bi(1) E(1) 84.60(8) (5) (3) (3) X(3) Bi(1) E(1) 80.73(8) 90.94(5) (4) (3) Page 23 of 27
24 Table S3. Selected bond lengths and angles of compounds 4a, a Bond lengths [Å] Bi(1) E(1) 2.874(5) 2.778(2) (10) (7) Bi(1) X(1) 2.509(4) (9) 2.523(2) (8) Bi(1) X(2 1 ) 2.693(5) (9) 2.763(2) (7) Bi(1) X(3) 2.482(5) (9) 2.485(2) (7) C(1) E(1) 1.827(6) 1.683(19) 1.703(9) 1.870(9) 1.866(6) Bond angles [ o ] (1) C(1) (1) 104.8(5) 104.1(15) 109.9(7) 106.3(7) 105.9(5) (1) C(1) E(1) 127.6(3) 131.3(12) 123.1(6) 129.0(7) 129.6(4) (2) C(1) E(1) 124.6(14) 130.2(6) 124.7(7) 124.5(4) X(1) Bi(1) X(2 1 ) 88.08(15) 90.64(3) 87.88(8) (2) X(1) Bi(1) E(1) 94.60(15) 93.55(5) 91.26(6) 97.88(2) X(3) Bi(1) X(1) 90.73(15) 90.08(3) 90.45(8) 88.10(3) X(3) Bi(1) X(2 1 ) 90.66(19) 93.52(3) 87.82(7) 87.30(2) X(3) Bi(1) E(1) 77.37(15) 81.18(5) 75.14(5) 79.27(2) E(1) Bi(1) X(2 1 ) (17) (5) (5) 90.05(2) C(1) E(1) Bi(1) 112.6(6) 110.8(3) 109.8(3) (19) Page 24 of 27
25 Table S4. Preparation of 4-chloropentylacetate. MeC 2.5 mol% catalyst DCM, RT, 2 h % Entry Catalyst Starting Material Conversion (%) a Yield (%) b 1 IPrS-BiBr 3 (7) IPrSe-Bi 3 (8) IPrSe-BiBr 3 (9) IPrTe-Bi 3 (10) IPrTe-BiBr 3 (11) IMesS-Bi 3 (12) IMesS-BiBr 3 (13) IMesSe-Bi 3 (14) IMesSe-BiBr 3 (15) IMesTe-Bi 3 (16) IMesTe-BiBr 3 (17) IPrS & Bi Bi BiBr Without catalyst 0 0 a The starting materials conversion was calculated after 2h. b % Yields were calculated based on the weight of products and the starting material conversion. Page 25 of 27
26 Table S5. Bismuth(III) mediated -acylative cleavage of different cyclic ethers. Entry Starting Materials Product Time (h) a Starting Material Conversion (%) Yiel d (%) c 1 Ph Me Me Me Me Me Ph Me Me Me Ph 6 Me Me b 12 7 Ph b 8 a = The obtimized time is 2h, however the reaction time was increased since the reaction was too slow. b =o further conversion after 48 h; c = % Yields were calculated based on the weight of the product with respect to the starting material. Page 26 of 27
27 Page 27 of 27 SI: Dr. GP, IITH
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