Carbonylation of 1-Lithiobutadiene with Carbon Monoxide Followed by Intramolecular Acyllithiation of C=C Double Bond and Intermolecular Acylation with Acid Chloride: Scope, Applications, and Mechanistic Aspects
Heng Li; Lantao Liu; Fei Zhao; Congyang Wang; Chao Wang; Qiuling Song; Wen-Xiong Zhang; Zhenfeng Xi; Journal of Organic Chemistry 77 (2012) 4793–4800; doi:10.1021/jo300631d

data_4027209
_publ_section_title
;
 Carbonylation of 1-Lithiobutadiene with Carbon Monoxide Followed by
 Intramolecular Acyllithiation of C=C Double Bond and Intermolecular
 Acylation with Acid Chloride: Scope, Applications, and Mechanistic
 Aspects
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4793
_journal_page_last               4800
_journal_paper_doi               10.1021/jo300631d
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C52 H62 Li2 O5'
_chemical_formula_sum            'C52 H62 Li2 O5'
_chemical_formula_weight         780.90
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                87.582(9)
_cell_angle_beta                 87.472(9)
_cell_angle_gamma                66.488(5)
_cell_formula_units_Z            2
_cell_length_a                   10.696(2)
_cell_length_b                   10.810(2)
_cell_length_c                   21.420(4)
_cell_measurement_reflns_used    6632
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.26
_cell_volume                     2268.0(7)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 ver 1.1'
_computing_publication_material  'SHELX97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_av_sigmaI/netI    0.0497
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            16863
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.27
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  0.9846
_exptl_absorpt_correction_T_min  0.9661
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.143
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.470
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.146
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     612
_refine_ls_number_reflns         7908
_refine_ls_number_restraints     170
_refine_ls_restrained_S_all      1.162
_refine_ls_R_factor_all          0.0943
_refine_ls_R_factor_gt           0.0823
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0594P)^2^+1.6432P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1783
_refine_ls_wR_factor_ref         0.1866
_reflns_number_gt                6896
_reflns_number_total             7908
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo300631d_si_004.cif
_cod_data_source_block           sa1594
_cod_original_cell_volume        2268.1(8)
_cod_database_code               4027209