Stereoselective Synthesis of o-Bromo (or Iodo)aryl P-Chirogenic Phosphines Based on Aryne Chemistry
Jérôme Bayardon; Hugo Laureano; Vincent Diemer; Mathieu Dutartre; Utpal Das; Yoann Rousselin; Jean-Christophe Henry; Françoise Colobert; Frédéric R. Leroux; Sylvain Jugé; Journal of Organic Chemistry 77 (2012) 5759–5769; doi:10.1021/jo300910w

data_4027280
_publ_contact_author_address
;
ICMUB
UMR 5260
CNRS - Univ. de Bourgogne
9 avenue AlainSavary
21078 Dijon Cedex
France
;
_publ_contact_author_email       Sylvain.Juge@u-bourgogne.fr
_publ_contact_author_fax         '+33 (0)3 80 39 60 98'
_publ_contact_author_name        'Sylvain Juge'
_publ_contact_author_phone       '+33 (0)3 80 39 61 13 '
_publ_section_title
;
 Stereoselective Synthesis of o-Bromo (or Iodo)aryl P-Chirogenic
 Phosphines Based on Aryne Chemistry
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5759
_journal_page_last               5769
_journal_paper_doi               10.1021/jo300910w
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C18 H29 B Br P'
_chemical_formula_sum            'C18 H29 B Br P'
_chemical_formula_weight         367.10
_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                 119.712(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.4399(2)
_cell_length_b                   14.7988(4)
_cell_length_c                   22.9356(5)
_cell_measurement_reflns_used    13782
_cell_measurement_temperature    115(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_volume                     3667.22(16)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'ORTEP3 (Farrugia,1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_diffrn_ambient_temperature      115(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_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  0.0589
_diffrn_reflns_av_sigmaI/netI    0.0855
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            23934
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.75
_exptl_absorpt_coefficient_mu    2.321
_exptl_absorpt_correction_T_max  0.5067
_exptl_absorpt_correction_T_min  0.4685
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Blessing, R. (1995) Acta Crystallogr., A51, 33-38'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1536
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.406
_refine_diff_density_min         -0.557
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.975
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     379
_refine_ls_number_reflns         8349
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.975
_refine_ls_R_factor_all          0.0908
_refine_ls_R_factor_gt           0.0448
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0442P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0854
_refine_ls_wR_factor_ref         0.0984
_reflns_number_gt                5447
_reflns_number_total             8349
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo300910w_si_003.cif
_cod_data_source_block           08jb219
_cod_original_cell_volume        3667.22(14)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4027280