Synthesis of α-Substituted Vinylsulfonium Salts and Their Application as Annulation Reagents in the Formation of Epoxide- and Cyclopropane-Fused Heterocycles.
Matlock, Johnathan V.; Fritz, Sven P.; Harrison, Stephen A.; Coe, Diane M.; McGarrigle, Eoghan M.; Aggarwal, Varinder K.; The Journal of organic chemistry 79 (2014) 10226–; doi:10.1021/jo501885z

data_4030049
_publ_section_title
;
 Synthesis of \a-Substituted Vinylsulfonium Salts and Their Application as
 Annulation Reagents in the Formation of Epoxide- and Cyclopropane-Fused
 Heterocycles.
;
_journal_issue                   21
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10226
_journal_paper_doi               10.1021/jo501885z
_journal_volume                  79
_journal_year                    2014
_chemical_formula_moiety         'C10 H13 S, B C24 H20'
_chemical_formula_sum            'C34 H33 B S'
_chemical_formula_weight         484.47
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 100.232(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   9.5938(4)
_cell_length_b                   36.4391(15)
_cell_length_c                   15.7075(7)
_cell_measurement_reflns_used    8404
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      19.78
_cell_measurement_theta_min      2.23
_cell_volume                     5403.8(4)
_computing_cell_refinement       'Bruker Apex2'
_computing_data_collection       'Bruker Apex2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker ShelXTL'
_computing_publication_material  'Bruker ShelXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_method       'phi and omega scans, 2 deg width'
_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  0.1928
_diffrn_reflns_av_sigmaI/netI    0.0889
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       47
_diffrn_reflns_limit_k_min       -47
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            176920
_diffrn_reflns_theta_full        27.71
_diffrn_reflns_theta_max         27.71
_diffrn_reflns_theta_min         1.43
_exptl_absorpt_coefficient_mu    0.141
_exptl_absorpt_correction_T_max  0.6468
_exptl_absorpt_correction_T_min  0.5065
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.191
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2064
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.18
_refine_diff_density_max         1.098
_refine_diff_density_min         -0.597
_refine_diff_density_rms         0.086
_refine_ls_extinction_coef       0.0048(4)
_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   1.122
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     654
_refine_ls_number_reflns         12532
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.122
_refine_ls_R_factor_all          0.1537
_refine_ls_R_factor_gt           0.1137
_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^)+(0.0000P)^2^+29.2267P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2260
_refine_ls_wR_factor_ref         0.2449
_reflns_number_gt                8797
_reflns_number_total             12532
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo501885z_si_002.cif
_cod_data_source_block           jm2110_0m
_cod_depositor_comments
'Adding full bibliography for 4030047--4030050.cif.'
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               4030049