Regioselective synthesis of functionalized 3,5-diketoesters and 2,4-diketosulfones by uncatalyzed condensation of 1-methoxy-1,3-bis(trimethylsilyloxy)-1,3-butadienes with α,β-unsaturated acid chlorides and sulfonyl chlorides
Rahn, Thomas; Dang, T. H. Tam; Spannenberg, Anke; Fischer, Christine; Langer, Peter; Organic & Biomolecular Chemistry 6 (2008) 3366–3370; doi:10.1039/b810151e

data_7151002
_publ_section_title
;
 Regioselective synthesis of functionalized 3,5-diketoesters and
 2,4-diketosulfones by uncatalyzed condensation of
 1-methoxy-1,3-bis(trimethylsilyloxy)-1,3-butadienes with
 \a,\b-unsaturated acid chlorides and sulfonyl chlorides
;
_journal_issue                   18
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_page_first              3366
_journal_page_last               3370
_journal_paper_doi               10.1039/b810151e
_journal_volume                  6
_journal_year                    2008
_chemical_formula_sum            'C11 H11 Cl O5 S'
_chemical_formula_weight         290.71
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 108.95(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.488(3)
_cell_length_b                   8.5440(17)
_cell_length_c                   10.372(2)
_cell_measurement_reflns_used    2000
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20
_cell_measurement_theta_min      4
_cell_volume                     1298.1(5)
_computing_cell_refinement       STOE-CELL
_computing_data_collection       STOE-EXPOSE
_computing_data_reduction        STOE-INTEGRATE
_computing_molecular_graphics    XP
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'STOE-IPDS I'
_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  0.0412
_diffrn_reflns_av_sigmaI/netI    0.0706
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4553
_diffrn_reflns_theta_full        25.96
_diffrn_reflns_theta_max         25.96
_diffrn_reflns_theta_min         2.76
_exptl_absorpt_coefficient_mu    0.464
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.331
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.852
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2525
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.852
_refine_ls_R_factor_all          0.0870
_refine_ls_R_factor_gt           0.0442
_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^)+(0.0554P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0979
_refine_ls_wR_factor_ref         0.1065
_reflns_number_gt                1438
_reflns_number_total             2525
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b810151e.txt
_cod_data_source_block           ks580m
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7151002