Synthesis of 1,3,5-Tricarbonyl Derivatives by Condensation of 1,3-Bis(silyl enol ethers) with Acid Chlorides
Thomas Rahn; Van T. H. Nguyen; T. H. Tam Dang; Zafar Ahmed; Karen Methling; Michael Lalk; Christine Fischer; Anke Spannenberg; Peter Langer; Journal of Organic Chemistry 72 (2007) 1957–1961; doi:10.1021/jo062153w

data_4022680
_publ_section_title
;
 Synthesis of 1,3,5-Tricarbonyl Derivatives by Condensation
 of 1,3-Bis(silyl enol ethers) with Acid Chlorides
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1957
_journal_page_last               1961
_journal_paper_doi               10.1021/jo062153w
_journal_volume                  72
_journal_year                    2007
_chemical_formula_sum            'C18 H18 O8'
_chemical_formula_weight         362.32
_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                 112.62(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.801(2)
_cell_length_b                   8.2176(16)
_cell_length_c                   11.755(2)
_cell_measurement_reflns_used    all
_cell_measurement_temperature    293(2)
_cell_volume                     873.9(3)
_computing_data_collection       STOE-X-AREA
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'STOE-IPDS II'
_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  0.0344
_diffrn_reflns_av_sigmaI/netI    0.0268
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13764
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.25
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.920
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     126
_refine_ls_number_reflns         2014
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.920
_refine_ls_R_factor_all          0.0570
_refine_ls_R_factor_gt           0.0367
_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^)+(0.0663P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0960
_refine_ls_wR_factor_ref         0.1017
_reflns_number_gt                1376
_reflns_number_total             2014
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo062153wsi20061017_094006.cif
_cod_data_source_block           ks487m
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4022680