Cycloaromatization Protocol for Synthesis of Polysubstituted Phenol Derivatives: Method Development and Mechanistic Studies
William T. Spencer; Alison J. Frontier; Journal of Organic Chemistry 77 (2012) 7730–7736; doi:10.1021/jo3010952

data_4027446
_publ_section_title
;
 Cycloaromatization Protocol for Synthesis of Polysubstituted Phenol
 Derivatives: Method Development and Mechanistic Studies
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7730
_journal_page_last               7736
_journal_paper_doi               10.1021/jo3010952
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C28 H26 O6'
_chemical_formula_sum            'C28 H26 O6'
_chemical_formula_weight         458.49
_chemical_name_common            frows01
_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                 91.566(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.897(3)
_cell_length_b                   16.638(4)
_cell_length_c                   12.533(3)
_cell_measurement_reflns_used    4003
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      34.82
_cell_measurement_theta_min      2.44
_cell_volume                     2271.4(10)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      100.0(1)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD Platform'
_diffrn_measurement_method       'area detector, \w scans per \f'
_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  0.0795
_diffrn_reflns_av_sigmaI/netI    0.0573
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            72911
_diffrn_reflns_theta_full        37.03
_diffrn_reflns_theta_max         37.03
_diffrn_reflns_theta_min         1.87
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.9851
_exptl_absorpt_correction_T_min  0.9563
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_description       needle
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.636
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     411
_refine_ls_number_reflns         11489
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0959
_refine_ls_R_factor_gt           0.0522
_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^)+(0.0692P)^2^+0.1616P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1251
_refine_ls_wR_factor_ref         0.1472
_reflns_number_gt                7203
_reflns_number_total             11489
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo3010952_si_002.cif
_cod_data_source_block           frows01
_cod_original_cell_volume        2271.5(10)
_cod_database_code               4027446