Mercury(II) Triflate-Catalyzed Cycloisomerization of Allenynes to Allenenes
So Hee Sim; Sang Ick Lee; Junhyeok Seo; Young Keun Chung; Journal of Organic Chemistry 72 (2007) 9818–9821; doi:10.1021/jo701591e

data_4023047
_publ_section_title
;
 Mercury(II) Triflate-Catalyzed Cycloisomerization
 of Allenynes to Allenenes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9818
_journal_page_last               9821
_journal_paper_doi               10.1021/jo701591e
_journal_volume                  72
_journal_year                    2007
_chemical_formula_sum            'C14 H15 N O2 S'
_chemical_formula_weight         261.0823
_chemical_name_systematic
;
 allenene
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 86.519(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.2166(6)
_cell_length_b                   14.528(3)
_cell_length_c                   14.394(3)
_cell_measurement_temperature    293(2)
_cell_volume                     1297.6(4)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    ORTEP32
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.831
_diffrn_measured_fraction_theta_max 0.831
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       '95mm CCD camera on \k-goniostat'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0674
_diffrn_reflns_av_sigmaI/netI    0.1030
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            4485
_diffrn_reflns_theta_full        27.67
_diffrn_reflns_theta_max         27.67
_diffrn_reflns_theta_min         1.99
_exptl_absorpt_coefficient_mu    0.061
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    0.334
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cubic
_exptl_crystal_F_000             138
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2517
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.1425
_refine_ls_R_factor_gt           0.0639
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0827P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1446
_refine_ls_wR_factor_ref         0.1791
_reflns_number_gt                1336
_reflns_number_total             2517
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo701591e-File002.cif
_cod_data_source_block           allene
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_original_formula_sum        'C14 H15 N1 O2 S1'
_cod_database_code               4023047