Nickel-Catalyzed Intermolecular [3 + 2 + 2] Cocyclization of Ethyl Cyclopropylideneacetate and Alkynes. Synthesis of Seven-Membered Carbocycles
Shinichi Saito; Shinsuke Komagawa; Isao Azumaya; Manami Masuda; Journal of Organic Chemistry 72 (2007) 9114–9120; doi:10.1021/jo7014714

data_4023019
_publ_contact_author_address
;Department of Chemistry, Faculty of Science,
 Tokyo University of Science,
 Kagurazaka, Shinjuku,
 Tokyo, Japan 162-8601
;
_publ_contact_author_email       ssaito@rs.kagu.tus.ac.jp
_publ_contact_author_name        'Shinichi Saito'
_publ_section_title
;
 Nickel-Catalyzed Intermolecular [3 + 2 + 2] Cocyclization
 of Ethyl Cyclopropylideneacetate and Alkynes. Synthesis of
 Seven-Membered Carbocycles
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9114
_journal_page_last               9120
_journal_paper_doi               10.1021/jo7014714
_journal_volume                  72
_journal_year                    2007
_chemical_formula_moiety         'C25 H26 O4 '
_chemical_formula_sum            'C25 H26 O4'
_chemical_formula_weight         390.48
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_cell_angle_alpha                90
_cell_angle_beta                 112.97(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.041(3)
_cell_length_b                   20.673(5)
_cell_length_c                   11.100(3)
_cell_measurement_temperature    296.2
_cell_measurement_theta_min      90.0
_cell_volume                     2121(1)
_computing_cell_refinement       'MSC/AFC Diffractometer Control'
_computing_data_collection       'MSC/AFC Diffractometer Control'
_computing_data_reduction        'teXsan Ver. 1.11'
_computing_publication_material  'teXsan Ver. 1.11'
_computing_structure_refinement  'teXsan Ver. 1.10'
_computing_structure_solution    SIR92
_diffrn_measured_fraction_theta_full 1.0038
_diffrn_measured_fraction_theta_max 1.0038
_diffrn_measurement_device_type  'Rigaku AFC5R'
_diffrn_measurement_method       \w-2\q
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.018
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4416
_diffrn_reflns_theta_full        72.63
_diffrn_reflns_theta_max         72.63
_diffrn_standards_decay_%        0.14
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.658
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_correction_T_min  0.851
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North, Phillips & Mathews, 1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.16
_refine_diff_density_min         -0.13
_refine_ls_extinction_coef       0.034(5)
_refine_ls_extinction_method     'Zachariasen(1967) type 2 Gaussian isotropic'
_refine_ls_goodness_of_fit_ref   1.437
_refine_ls_hydrogen_treatment    noref
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3769
_refine_ls_R_factor_gt           0.0434
_refine_ls_shift/su_max          0.0003
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[\s^2^(Fo) + 0.00090|Fo|^2^]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0712
_reflns_number_gt                2898
_reflns_number_total             4241
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            jo7014714-File003.cif
_cod_data_source_block           sk2-016-d
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_original_formula_sum        'C25 H26 O4 '
_cod_database_code               4023019