Chemoselective synthesis of highly substituted 1,2-allenyl ketones, furans, and 2-alkynyl ketones from reaction of lithium selenolates with 1-(1-alkynyl)cyclopropyl ketones and electrophiles.
Xu, Jianfeng; Zhu, Shugao; Wu, Luling; Huang, Xian; Organic & biomolecular chemistry 10 (2012) 3705–3714; doi:10.1039/c2ob25071c

data_7152316
_publ_section_title
;
 Chemoselective synthesis of highly substituted 1,2-allenyl ketones,
 furans, and 2-alkynyl ketones from reaction of lithium selenolates with
 1-(1-alkynyl)cyclopropyl ketones and electrophiles.
;
_journal_issue                   18
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3705
_journal_page_last               3714
_journal_paper_doi               10.1039/c2ob25071c
_journal_volume                  10
_journal_year                    2012
_chemical_formula_moiety         'C25 H21 I O Se'
_chemical_formula_sum            'C25 H21 I O Se'
_chemical_formula_weight         543.28
_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   constr
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 106.365(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.1185(6)
_cell_length_b                   5.7251(2)
_cell_length_c                   24.3065(9)
_cell_measurement_reflns_used    3569
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.3475
_cell_measurement_theta_min      2.7142
_cell_volume                     2152.13(14)
_computing_cell_refinement       'CrysAlis PRO (Oxford Diffraction, 2009)'
_computing_data_collection       'CrysAlis PRO'
_computing_data_reduction        'CrysAlis PRO'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  OLEX2
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_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  0.0326
_diffrn_reflns_av_sigmaI/netI    0.0424
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            9508
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         2.72
_exptl_absorpt_coefficient_mu    3.192
_exptl_absorpt_correction_T_max  0.727
_exptl_absorpt_correction_T_min  0.638
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis PRO (Oxford Diffraction, 2009)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.677
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.732
_refine_diff_density_min         -0.618
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3928
_refine_ls_number_restraints     187
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0368
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0375P)^2^+1.5711P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0816
_refine_ls_wR_factor_ref         0.0921
_reflns_number_gt                2996
_reflns_number_total             3928
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ob25071c.txt
_cod_data_source_block           101110_jeff_086
_cod_original_cell_volume        2152.12(14)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7152316