2,3,4- or 2,3,5-Trisubstituted Furans: Catalyst-Controlled Highly Regioselective Ring-Opening Cycloisomerization Reaction of Cyclopropenyl Ketones
Shengming Ma; Junliang Zhang; Journal of the American Chemical Society 125 (2003) 12386–12387; doi:10.1021/ja036616g

data_4114252
_publ_section_title
;
 2,3,4- or 2,3,5-Trisubstituted Furans: Catalyst-Controlled Highly
 Regioselective Ring-Opening Cycloisomerization Reaction of Cyclopropenyl
 Ketones
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12386
_journal_page_last               12387
_journal_paper_doi               10.1021/ja036616g
_journal_volume                  125
_journal_year                    2003
_chemical_formula_sum            'C15 H18 O3 S'
_chemical_formula_weight         278.35
_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                68.445(2)
_cell_angle_beta                 81.980(3)
_cell_angle_gamma                66.606(2)
_cell_formula_units_Z            2
_cell_length_a                   7.9303(11)
_cell_length_b                   9.6961(13)
_cell_length_c                   11.1246(15)
_cell_measurement_reflns_used    1425
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      48.104
_cell_measurement_theta_min      5.107
_cell_volume                     730.16(17)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.903
_diffrn_measured_fraction_theta_max 0.903
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0589
_diffrn_reflns_av_sigmaI/netI    0.0587
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4497
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         1.97
_exptl_absorpt_coefficient_mu    0.223
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47329
_exptl_absorpt_correction_type   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.670
_exptl_crystal_size_mid          0.462
_exptl_crystal_size_min          0.152
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.010(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.911
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3261
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      0.911
_refine_ls_R_factor_all          0.0708
_refine_ls_R_factor_gt           0.0488
_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^)+(0.0553P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1119
_refine_ls_wR_factor_ref         0.1212
_reflns_number_gt                2119
_reflns_number_total             3261
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja036616gsi20030611_083518.cif
_cod_data_source_block           cd2366
_cod_database_code               4114252