Ruthenium-Catalyzed Reactions of 1-Cyclopropyl-2-propyn-1-ols with Anilines and Water via Allenylidene Intermediates: Selective Preparation of Tri- and Tetrasubstituted Conjugated Enynes
Yoshihiro Yamauchi; Gen Onodera; Ken Sakata; Masahiro Yuki; Yoshihiro Miyake; Sakae Uemura; Yoshiaki Nishibayashi; Journal of the American Chemical Society 129 (2007) 5175–5179; doi:10.1021/ja0687926

data_4109329
_publ_section_title
;
 Ruthenium-Catalyzed Reactions of 1-Cyclopropyl-2-propyn-1-ols with
 Anilines and Water via Allenylidene Intermediates: Selective Preparation
 of Tri- and Tetrasubstituted Conjugated Enynes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5175
_journal_page_last               5179
_journal_paper_doi               10.1021/ja0687926
_journal_volume                  129
_journal_year                    2007
_chemical_formula_moiety         'C19 H19 N O '
_chemical_formula_sum            'C19 H19 N O'
_chemical_formula_weight         277.37
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_audit_creation_date             2006-11-07
_audit_creation_method           'by CrystalStructure 3.7.0'
_cell_angle_alpha                90.0000
_cell_angle_beta                 108.488(2)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   11.4362(7)
_cell_length_b                   8.1087(5)
_cell_length_c                   17.7590(19)
_cell_measurement_reflns_used    6734
_cell_measurement_temperature    173.1
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      2.4
_cell_volume                     1561.8(2)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.7.0'
_computing_structure_refinement  CRYSTALS
_computing_structure_solution    SIR97
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.078
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            12556
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.728
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
    Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.179
_exptl_crystal_description       platelet
_exptl_crystal_F_000             592.00
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.36
_refine_diff_density_min         -0.33
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     266
_refine_ls_number_reflns         3545
_refine_ls_R_factor_gt           0.0574
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[0.0004Fo^2^ + 1.0000\s(Fo^2^)]/(4Fo^2^)'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1190
_reflns_number_gt                1920
_reflns_number_total             3547
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ja0687926si20061208_070539.cif
_cod_data_source_block           '_YY-1-OMe_________________'
_cod_original_formula_sum        'C19 H19 N O '
_cod_database_code               4109329