Iodine(III)-Mediated Umpolung of Bromide Salts for the Ethoxybromination of Enamides.
Nocquet-Thibault, Sophie; Retailleau, Pascal; Cariou, Kevin; Dodd, Robert H.; Organic letters 15 (2013) 1842–1845; doi:10.1021/ol400453b

data_1511908
_publ_section_title
;
 Iodine(III)-Mediated Umpolung of Bromide Salts for the Ethoxybromination
 of Enamides.
;
_journal_issue                   8
_journal_name_full               'Organic letters'
_journal_page_first              1842
_journal_page_last               1845
_journal_paper_doi               10.1021/ol400453b
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C23 H24 Br N O3 S'
_chemical_formula_sum            'C23 H24 Br N O3 S'
_chemical_formula_weight         474.40
_chemical_name_systematic
; 
 rac (2R,3R)
2-bromo-1-ethoxy-2-phenylethyl)-4-methyl-N-phenylbenzenesulfonamide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 103.389(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   24.175(5)
_cell_length_b                   15.224(3)
_cell_length_c                   12.249(2)
_cell_measurement_reflns_used    4967
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.261
_cell_measurement_theta_min      0.407
_cell_volume                     4385.6(14)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997); COLLECT (Nonius B.V., 1999)'
_computing_data_collection
'DENZO (Otwinowski & Minor, 1997); COLLECT (Nonius B.V., 1999)'
_computing_data_reduction        'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement
'SHELXL97 (Sheldrick, 2008); CRYSTALBUILDER (Welter, 2006)'
_computing_structure_solution    'SIR97 (Altomare et al, 1999)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Nonius kappa-CCD diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0472
_diffrn_reflns_av_sigmaI/netI    0.0587
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            30678
_diffrn_reflns_theta_full        21.33
_diffrn_reflns_theta_max         21.33
_diffrn_reflns_theta_min         0.87
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Nonius Kappa CCD'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.994
_exptl_absorpt_correction_T_max  0.89
_exptl_absorpt_correction_T_min  0.61
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Scalepack (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             1952
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.764
_refine_diff_density_min         -0.602
_refine_diff_density_rms         0.200
_refine_ls_extinction_coef       0.0089(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.470
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     525
_refine_ls_number_reflns         4863
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.470
_refine_ls_R_factor_all          0.1471
_refine_ls_R_factor_gt           0.1070
_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^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3274
_refine_ls_wR_factor_ref         0.3654
_reflns_number_gt                3444
_reflns_number_total             4863
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol400453b_si_002.cif
_cod_data_source_block           compound_2
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1511908