Direct Synthesis of B-Allyl and B-Allenyldiisopinocampheylborane Reagents Using Allyl or Propargyl Halides and Indium Metal Under Barbier-Type Conditions
Lacie C. Hirayama; Terra D. Haddad; Allen G. Oliver; Bakthan Singaram; Journal of Organic Chemistry 77 (2012) 4342–4353; doi:10.1021/jo300260a

data_4027173
_publ_contact_author_address     '378 PSB'
_publ_contact_author_email       hirayama@chemsitry.ucsc.edu
_publ_contact_author_name        'Lacie Hirayama'
_publ_contact_author_phone       9-3479
_publ_section_title
;
 Direct Synthesis of B-Allyl and B-Allenyldiisopinocampheylborane Reagents
 Using Allyl or Propargyl Halides and Indium Metal Under Barbier-Type
 Conditions
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4342
_journal_page_last               4353
_journal_paper_doi               10.1021/jo300260a
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C16 H32 Br2 Cl2 In2 O4'
_chemical_formula_sum            'C16 H32 Br2 Cl2 In2 O4'
_chemical_formula_weight         748.78
_chemical_name_systematic
; 
 ? 
;
_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                 95.853(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.393(2)
_cell_length_b                   10.5060(17)
_cell_length_c                   15.698(3)
_cell_measurement_reflns_used    7411
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.85
_cell_measurement_theta_min      2.33
_cell_volume                     2525.4(7)
_computing_cell_refinement       'Bruker SAINT v7.34'
_computing_data_collection       'Bruker APEX-II v2.1'
_computing_data_reduction        'Bruker SAINT v7.34'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153(2)
_diffrn_detector_area_resol_mean 83.33
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       \w/2\q-scans
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_sigmaI/netI    0.0225
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            21951
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.34
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.219
_exptl_absorpt_correction_T_max  0.6509
_exptl_absorpt_correction_T_min  0.3228
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Sheldrick, 2004'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.969
_exptl_crystal_description       block
_exptl_crystal_F_000             1448
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.874
_refine_diff_density_min         -1.297
_refine_diff_density_rms         0.108
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         5154
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0433
_refine_ls_shift/su_max          0.027
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0516P)^2^+8.9414P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1082
_refine_ls_wR_factor_ref         0.1186
_reflns_number_gt                4013
_reflns_number_total             5154
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo300260a_si_001.cif
_cod_data_source_block           xsc07023
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4027173