Chemoselective synthesis of tetrasubstituted furans via intramolecular Wittig reactions: mechanism and theoretical analysis.
Lee, Yu-Ting; Lee, Yen-Te; Lee, Chia-Jui; Sheu, Chia-Ning; Lin, Bo-Yu; Wang, Jeng-Han; Lin, Wenwei; Organic & biomolecular chemistry 11 (2013) 5156–5161; doi:10.1039/c3ob40858b

data_7153024
_publ_section_title
;
 Chemoselective synthesis of tetrasubstituted furans via intramolecular
 Wittig reactions: mechanism and theoretical analysis.
;
_journal_issue                   31
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5156
_journal_page_last               5161
_journal_paper_doi               10.1039/c3ob40858b
_journal_volume                  11
_journal_year                    2013
_chemical_formula_moiety         'C28 H22 Br N O3'
_chemical_formula_sum            'C28 H22 Br N O3'
_chemical_formula_weight         500.38
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                67.414(12)
_cell_angle_beta                 89.449(9)
_cell_angle_gamma                67.009(8)
_cell_formula_units_Z            4
_cell_length_a                   12.4196(15)
_cell_length_b                   13.915(2)
_cell_length_c                   17.027(2)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     2466.7(6)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.955
_diffrn_measured_fraction_theta_max 0.955
_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  0.0757
_diffrn_reflns_av_sigmaI/netI    0.1658
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            18122
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         1.81
_exptl_absorpt_coefficient_mu    1.695
_exptl_absorpt_correction_T_max  0.8763
_exptl_absorpt_correction_T_min  0.4613
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.950
_refine_diff_density_min         -0.736
_refine_diff_density_rms         0.098
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.975
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     599
_refine_ls_number_reflns         8323
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.975
_refine_ls_R_factor_all          0.2041
_refine_ls_R_factor_gt           0.0821
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1355P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2058
_refine_ls_wR_factor_ref         0.2642
_reflns_number_gt                3485
_reflns_number_total             8323
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ob40858b.txt
_cod_data_source_block           a12767
_cod_original_cell_volume        2466.8(6)
_cod_database_code               7153024