Efficient one-pot synthesis of polyfunctionalized thiophenes via an amine-mediated ring opening of EWG-activated 2-methylene-1,3-dithioles.
Liang, Fushun; Li, Dazhi; Zhang, Lei; Gao, Jingjie; Liu, Qun; Organic letters 9 (2007) 4845–4848; doi:10.1021/ol7021752

data_1505593
_publ_section_title
;
 Efficient one-pot synthesis of polyfunctionalized thiophenes via an
 amine-mediated ring opening of EWG-activated 2-methylene-1,3-dithioles.
;
_journal_issue                   23
_journal_name_full               'Organic letters'
_journal_page_first              4845
_journal_page_last               4848
_journal_paper_doi               10.1021/ol7021752
_journal_volume                  9
_journal_year                    2007
_chemical_formula_sum            'C11 H15 N O2 S'
_chemical_formula_weight         225.31
_chemical_name_systematic
; 
 ? 
;
_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                 96.859(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.4217(9)
_cell_length_b                   19.233(3)
_cell_length_c                   10.9100(19)
_cell_measurement_temperature    273(2)
_cell_volume                     1129.5(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.0256
_diffrn_reflns_av_sigmaI/netI    0.0300
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6252
_diffrn_reflns_theta_full        26.04
_diffrn_reflns_theta_max         26.04
_diffrn_reflns_theta_min         2.12
_exptl_absorpt_coefficient_mu    0.266
_exptl_absorpt_correction_T_max  0.974
_exptl_absorpt_correction_T_min  0.969
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             480.0
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.027
_refine_diff_density_min         -0.699
_refine_diff_density_rms         0.098
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_matrix_type           full
_refine_ls_number_parameters     141
_refine_ls_number_reflns         2218
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.1007
_refine_ls_R_factor_gt           0.0848
_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^)+(0.1616P)^2^+1.7649P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2536
_refine_ls_wR_factor_ref         0.2741
_reflns_number_gt                1748
_reflns_number_total             2218
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol7021752-file003.cif
_cod_data_source_block           2a
_cod_original_sg_symbol_H-M      P21/n
_cod_original_formula_sum        'C11 H15 N O2 S '
_cod_database_code               1505593