Sulfur Monoxide Transfer from peri-Substituted Trisulfide-2-oxides to Dienes: Substituent Effects, Mechanistic Studies and Application in Thiophene Synthesis
Richard S. Grainger; Bhaven Patel; Benson M. Kariuki; Louise Male; Neil Spencer; Journal of the American Chemical Society 133 (2011) 5843–5852; doi:10.1021/ja108865w

data_4105932
_publ_contact_author
;
Dr B.M. Kariuki
School of Chemistry, Cardiff University
Main Building
Park Place
Cardiff
CF10 3AT
;
_publ_contact_author_email       kariukib@cf.ac.uk
_publ_section_title
;
 Sulfur Monoxide Transfer from peri-Substituted Trisulfide-2-oxides to
 Dienes: Substituent Effects, Mechanistic Studies and Application in
 Thiophene Synthesis
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5843
_journal_page_last               5852
_journal_paper_doi               10.1021/ja108865w
_journal_volume                  133
_journal_year                    2011
_chemical_formula_moiety         'C12 H10 Br2 O2'
_chemical_formula_sum            'C12 H10 Br2 O2'
_chemical_formula_weight         346.02
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                84.2050(10)
_cell_angle_beta                 89.146(2)
_cell_angle_gamma                85.231(2)
_cell_formula_units_Z            4
_cell_length_a                   7.3022(2)
_cell_length_b                   7.6899(2)
_cell_length_c                   21.1997(7)
_cell_measurement_reflns_used    41509
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     1180.22(6)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_data_reduction
'EvalCCD (Duisenberg, Kroon-Batenburg, Schreurs, 2003)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution
;
SIR92 (Altomare, Cascarano, Giacovazzo, Guagliardi, Burla, Polidori, 
Camalli, 1994)
;
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean '4096x4096pixels / 62x62mm'
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type
'Bruker-Nonius APEX II CCD camera on \k-goniostat'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  '10cm confocal mirrors'
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0245
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            5376
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         3.14
_exptl_absorpt_coefficient_mu    6.849
_exptl_absorpt_correction_T_max  0.7713
_exptl_absorpt_correction_T_min  0.4070
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'TWINABS (Sheldrick, G.M., 2007)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.947
_exptl_crystal_description       Rod
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.417
_refine_diff_density_min         -2.144
_refine_diff_density_rms         0.361
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.159
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         5376
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.159
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0594
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0908P)^2^+9.1774P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1650
_refine_ls_wR_factor_ref         0.1733
_reflns_number_gt                5069
_reflns_number_total             5376
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja108865w_si_006.cif
_cod_data_source_block           45
_cod_database_code               4105932