Tandem Vinylogous 1,2-Addition/Anionic Oxy-Cope Reaction Leading from Butadiene Sulfone to an Orthogonally Functionalized Bicycle
Michael G. Brant; Caleb M. Bromba; Jeremy E. Wulff; Journal of Organic Chemistry 75 (2010) 6312–6315; doi:10.1021/jo101389c

data_4025686
_publ_contact_author_address
'Dept. of Chemistry.  University of Victoria B.C.'
_publ_contact_author_email       wulff@uvic.ca
_publ_contact_author_name        'Jeremy Wulff'
_publ_section_title
;
 Tandem Vinylogous 1,2-Addition/Anionic Oxy-Cope Reaction Leading from
 Butadiene Sulfone to an Orthogonally Functionalized Bicycle
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6312
_journal_page_last               6315
_journal_paper_doi               10.1021/jo101389c
_journal_volume                  75
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C11 H16 O3 S'
_chemical_formula_sum            'C11 H16 O3 S'
_chemical_formula_weight         228.30
_space_group_IT_number           43
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'F 2 -2d'
_symmetry_space_group_name_H-M   'F d d 2'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   12.0282(1)
_cell_length_b                   34.3106(6)
_cell_length_c                   11.2526(1)
_cell_measurement_reflns_used    6726
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      69.27
_cell_measurement_theta_min      2.58
_cell_volume                     4643.89(10)
_computing_cell_refinement       'Bruker SAINT v7.60A'
_computing_data_collection       'Bruker APEX-II v2009-9'
_computing_data_reduction        'Bruker SAINT v7.60A'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 83.33
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX'
_diffrn_measurement_method       'combination of \w and \f-scans '
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_sigmaI/netI    0.0234
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10959
_diffrn_reflns_theta_full        69.57
_diffrn_reflns_theta_max         69.57
_diffrn_reflns_theta_min         5.16
_exptl_absorpt_coefficient_mu    2.371
_exptl_absorpt_correction_T_max  0.8322
_exptl_absorpt_correction_T_min  0.6657
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS, Sheldrick, 2008'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1952
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.070(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         2113
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0264
_refine_ls_R_factor_gt           0.0260
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0405P)^2^+3.1346P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0666
_refine_ls_wR_factor_ref         0.0669
_reflns_number_gt                2080
_reflns_number_total             2113
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo101389c_si_001.cif
_cod_data_source_block           uvic01
_cod_database_code               4025686