Pd(0)-Catalyzed [1,5]-Sigmatropic Hydrogen Shift of Propargylic Esters toward Substituent Naphthylamines
Shu-Chun Zhao; Xing-Zhong Shu; Ke-Gong Ji; An-Xi Zhou; Ting He; Xue-Yuan Liu; Yong-Min Liang; Journal of Organic Chemistry 76 (2011) 1941–1944; doi:10.1021/jo1024267

data_4026128
_publ_section_title
;
 Pd(0)-Catalyzed [1,5]-Sigmatropic Hydrogen Shift of Propargylic Esters
 toward Substituent Naphthylamines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1941
_journal_page_last               1944
_journal_paper_doi               10.1021/jo1024267
_journal_volume                  76
_journal_year                    2011
_chemical_formula_sum            'C20 H17 N O'
_chemical_formula_weight         287.35
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.5130(3)
_cell_length_b                   12.6052(3)
_cell_length_c                   19.5281(5)
_cell_measurement_reflns_used    2210
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.27
_cell_measurement_theta_min      2.52
_cell_volume                     3080.15(13)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w 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  0.0508
_diffrn_reflns_av_sigmaI/netI    0.0333
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14803
_diffrn_reflns_theta_full        24.65
_diffrn_reflns_theta_max         24.65
_diffrn_reflns_theta_min         2.09
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.9864
_exptl_absorpt_correction_T_min  0.9805
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            coloeless
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_description       block
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       0.0031(6)
_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   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2603
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0673
_refine_ls_R_factor_gt           0.0390
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0470P)^2^+0.3037P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0892
_refine_ls_wR_factor_ref         0.1031
_reflns_number_gt                1777
_reflns_number_total             2603
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo1024267_si_001.cif
_cod_data_source_block           pbca
_cod_database_code               4026128