Syntheses of 3,4-Disubstituted Pyrroles and Furans via Lewis Acid-Promoted Semipinacol Rearrangement/Alkyne-Ketone Metathesis Reaction of (C)-2-N- or O-((3-Arylpropargyl)methyl)-Tethered 3,5,5-Trimethyl-2,3-epoxycyclohexan-1-ones
Ming-Chang P. Yeh; Ming-Nan Lin; Ching-Hsien Hsu; Chia-Jung Liang; Journal of Organic Chemistry 78 (2013) 12381–12396; doi:10.1021/jo402025z

data_4028840
_publ_section_title
;
 Syntheses of 3,4-Disubstituted Pyrroles and Furans via Lewis
 Acid-Promoted Semipinacol Rearrangement/Alkyne-Ketone Metathesis Reaction
 of (C)-2-N- or O-((3-Arylpropargyl)methyl)-Tethered
 3,5,5-Trimethyl-2,3-epoxycyclohexan-1-ones
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              12381
_journal_page_last               12396
_journal_paper_doi               10.1021/jo402025z
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C23 H23 Cl2 N O3 S'
_chemical_formula_sum            'C23 H23 Cl2 N O3 S'
_chemical_formula_weight         464.38
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 91.813(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   26.8945(5)
_cell_length_b                   7.7214(2)
_cell_length_c                   20.9187(5)
_cell_measurement_reflns_used    13632
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      25.028
_cell_measurement_theta_min      2.037
_cell_volume                     4341.87(17)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction        'HKL Denzo and Scalepack'
_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_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_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  0.0527
_diffrn_reflns_av_sigmaI/netI    0.0387
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            12147
_diffrn_reflns_theta_full        25.04
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_min         2.43
_exptl_absorpt_coefficient_mu    0.421
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_correction_T_min  0.8723
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 ?
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_description       prism
_exptl_crystal_F_000             1936
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.501
_refine_diff_density_min         -0.528
_refine_diff_density_rms         0.136
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3819
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.114
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0402
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0749P)^2^+2.8680P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1141
_refine_ls_wR_factor_ref         0.1303
_reflns_number_gt                3219
_reflns_number_total             3819
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo402025z_si_004.cif
_cod_data_source_block           12883
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4028840