Regioselective Hydronickelation of Allenes and Its Application to the Hydrocyanative Carbocyclization Reaction of Allene-Ynes and Bis-Allenes
Yuka Amako; Hiroto Hori; Shigeru Arai; Atsushi Nishida; Journal of Organic Chemistry 78 (2013) 10763–10775; doi:10.1021/jo401758v

data_4028717
_publ_section_title
;
 Regioselective Hydronickelation of Allenes and Its Application to the
 Hydrocyanative Carbocyclization Reaction of Allene-Ynes and Bis-Allenes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              10763
_journal_page_last               10775
_journal_paper_doi               10.1021/jo401758v
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C19 H24 N2 O4 S'
_chemical_formula_weight         376.46
_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                 91.745(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.0701(17)
_cell_length_b                   10.7138(16)
_cell_length_c                   15.567(2)
_cell_measurement_reflns_used    6575
_cell_measurement_temperature    173
_cell_measurement_theta_max      28.19
_cell_measurement_theta_min      2.62
_cell_volume                     1845.4(5)
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.863
_diffrn_measured_fraction_theta_max 0.863
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0313
_diffrn_reflns_av_sigmaI/netI    0.0396
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9108
_diffrn_reflns_theta_full        28.47
_diffrn_reflns_theta_max         28.47
_diffrn_reflns_theta_min         2.31
_exptl_absorpt_coefficient_mu    0.203
_exptl_absorpt_correction_T_max  0.9417
_exptl_absorpt_correction_T_min  0.9055
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS Sheldrick 1996
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.657
_refine_diff_density_min         -0.476
_refine_diff_density_rms         0.110
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.783
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         4029
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.783
_refine_ls_R_factor_all          0.0626
_refine_ls_R_factor_gt           0.0578
_refine_ls_shift/su_max          0.069
_refine_ls_shift/su_mean         0.005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2085
_refine_ls_wR_factor_ref         0.2187
_reflns_number_gt                3614
_reflns_number_total             4029
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo401758v_si_003.cif
_cod_data_source_block           a130322hoshi1-2m
_cod_original_sg_symbol_H-M      'P 1 21/c 1 '
_cod_database_code               4028717