Studies on Electrophilic Reaction of Tertiary 2,3-Allenols with NBS in H2O or Aqueous MeCN: An Efficient Selective Synthesis of 2-Bromoallylic Ketones, 1,2-Allenyl Ketones, or 3-Bromo-2,5-dihydrofurans
Jing Li; Wangqing Kong; Yihua Yu; Chunling Fu; Shengming Ma; Journal of Organic Chemistry 74 (2009) 8733–8738; doi:10.1021/jo9018717

data_4025049
_publ_section_title
;
Studies on Electrophilic Reaction of Tertiary 2,3-Allenols with NBS in H2O
or Aqueous MeCN: An Efficient Selective Synthesis of 2-Bromoallylic
Ketones, 1,2-Allenyl Ketones, or 3-Bromo-2,5-dihydrofurans
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8733
_journal_page_last               8738
_journal_paper_doi               10.1021/jo9018717
_journal_volume                  74
_journal_year                    2009
_chemical_formula_sum            'C13 H13 Br O'
_chemical_formula_weight         265.14
_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                 99.934(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.7860(4)
_cell_length_b                   6.0794(2)
_cell_length_c                   14.2698(4)
_cell_measurement_temperature    173(2)
_cell_volume                     1092.58(6)
_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_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  0.0389
_diffrn_reflns_av_sigmaI/netI    0.0266
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9937
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.98
_exptl_absorpt_coefficient_mu    3.731
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.254839
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.612
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.764
_exptl_crystal_size_mid          0.702
_exptl_crystal_size_min          0.404
_refine_diff_density_max         0.455
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       0.0176(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1922
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0216
_refine_ls_R_factor_gt           0.0204
_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^)+(0.0206P)^2^+0.8397P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0516
_refine_ls_wR_factor_ref         0.0524
_reflns_number_gt                1831
_reflns_number_total             1922
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9018717_si_001.cif
_cod_data_source_block           z
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4025049