Synthesis of 2-(Trifluoromethyl)oxazoles from β-Monosubstituted Enamines via PhI(OCOCF3)2-Mediated Trifluoroacetoxylation and Cyclization
Feifei Zhao; Xin Liu; Rui Qi; Daisy Zhang-Negrerie; Jianhui Huang; Yunfei Du; Kang Zhao; Journal of Organic Chemistry 76 (2011) 10338–10344; doi:10.1021/jo202070h

data_4026810
_publ_section_title
;
 Synthesis of 2-(Trifluoromethyl)oxazoles from \b-Monosubstituted Enamines
 via PhI(OCOCF3)2-Mediated Trifluoroacetoxylation and Cyclization
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              10338
_journal_page_last               10344
_journal_paper_doi               10.1021/jo202070h
_journal_volume                  76
_journal_year                    2011
_chemical_formula_moiety         'C12 H8 F3 N O3'
_chemical_formula_sum            'C12 H8 F3 N O3'
_chemical_formula_weight         271.19
_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                 126.37(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.925(2)
_cell_length_b                   8.6147(17)
_cell_length_c                   15.619(5)
_cell_measurement_reflns_used    2895
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.89
_cell_measurement_theta_min      2.35
_cell_volume                     1183.6(6)
_computing_cell_refinement       RAPID-AUTO
_computing_data_collection       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2002)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku/MSC Mercury CCD'
_diffrn_measurement_method       \w
_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  0.0450
_diffrn_reflns_av_sigmaI/netI    0.0392
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9723
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.02
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.140
_exptl_absorpt_correction_T_max  0.9712
_exptl_absorpt_correction_T_min  0.9592
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Jacobson, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.522
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.782
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.193
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2319
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.545
_refine_ls_R_factor_all          0.1304
_refine_ls_R_factor_gt           0.0756
_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^)+(0.0798P)^2^+0.8788P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1941
_refine_ls_wR_factor_ref         0.2353
_reflns_number_gt                1182
_reflns_number_total             2319
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo202070h_si_002.cif
_cod_data_source_block           1
_cod_original_cell_volume        1183.6(5)
_cod_original_sg_symbol_H-M      'P 21/c '
_cod_database_code               4026810