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_4027208
_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         'C21 H27 I O2'
_chemical_formula_sum            'C21 H27 I O2'
_chemical_formula_weight         438.33
_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                 131.633(18)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.119(2)
_cell_length_b                   12.595(3)
_cell_length_c                   17.064(5)
_cell_measurement_reflns_used    768
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.17
_cell_volume                     1946.7(10)
_computing_cell_refinement       'Rapid Auto(Rigaku 2001)'
_computing_data_collection       'Rapid Auto(Rigaku 2001)'
_computing_data_reduction        'Rapid Auto(Rigaku 2001)'
_computing_molecular_graphics    'XP in Siemens SHELXTL (Sheldrick, 1994)'
_computing_publication_material  'SHELX97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku raxis Rapid IP Area Detector'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0179
_diffrn_reflns_av_sigmaI/netI    0.0304
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6562
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.25
_exptl_absorpt_coefficient_mu    1.655
_exptl_absorpt_correction_T_max  0.5646
_exptl_absorpt_correction_T_min  0.4917
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR by T.Higashi    8 March, 1995'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_description       block
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.49
_exptl_crystal_size_min          0.39
_refine_diff_density_max         2.499
_refine_diff_density_min         -0.740
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.228
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3626
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.228
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0501
_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^)+(0.0305P)^2^+4.8489P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0954
_refine_ls_wR_factor_ref         0.0995
_reflns_number_gt                3278
_reflns_number_total             3626
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo300631d_si_003.cif
_cod_data_source_block           a
_cod_original_cell_volume        1946.7(8)
_cod_database_code               4027208