Cyclopropyl Alkynes as Mechanistic Probes to Distinguish Between Vinyl Radical and Ionic Intermediates
Gottschling, Stephen E.; Grant, Tina N.; Milnes, Kaarina K.; Jennings, Michael, C.; Baines, Kim M.; Journal of Organic Chemistry 70 (2005) 2686–2695; doi:10.1021/jo047797n

data_4020086
_publ_section_title
;
Cyclopropyl Alkynes as Mechanistic Probes to Distinguish
Between Vinyl Radical and Ionic Intermediates
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2686
_journal_page_last               2695
_journal_paper_doi               10.1021/jo047797n
_journal_volume                  70
_journal_year                    2005
_chemical_absolute_configuration ad
_chemical_formula_sum            'C13 H14 Br2 O'
_chemical_formula_weight         346.06
_chemical_melting_point          68.0
_chemical_name_systematic
;
 1,1-Dibromo-2-(trans,trans-2-methoxy-1-methyl-3-phenylcyclopropyl)ethene
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.5473(2)
_cell_length_b                   10.8620(3)
_cell_length_c                   18.6055(6)
_cell_measurement_reflns_used    1759
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.55
_cell_volume                     1323.16(7)
_diffrn_ambient_temperature      297(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measurement_device_type  'Nonius Kappa-CCD'
_diffrn_measurement_method       '\f scans, and \w scans with \k offsets'
_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  0.1030
_diffrn_reflns_av_sigmaI/netI    0.0397
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            12802
_diffrn_reflns_theta_max         24.70
_diffrn_reflns_theta_min         2.88
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    6.104
_exptl_absorpt_correction_T_max  0.603
_exptl_absorpt_correction_T_min  0.073
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO-SMN (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.737
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       chip
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.49
_exptl_crystal_size_min          0.10
_refine_ls_abs_structure_details 'Flack (1983), 676 Friedel pairs'
_refine_ls_abs_structure_Flack   0.56(3)
_refine_ls_extinction_coef       0.027(3)
_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   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     135
_refine_ls_number_reflns         2251
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0788
_refine_ls_R_factor_gt           0.0611
_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^)+(0.1023P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1403
_refine_ls_wR_factor_ref         0.1512
_reflns_number_gt                1805
_reflns_number_total             2251
_reflns_threshold_expression     I>2sigma(I)
_cod_database_code               4020086