N-Tosyloxycarbamates as a Source of Metal Nitrenes: Rhodium-Catalyzed C-H Insertion and Aziridination Reactions
Hélène Lebel; Kim Huard; Sylvain Lectard; Journal of the American Chemical Society 127 (2005) 14198–14199; doi:10.1021/ja0552850

data_4112027
_publ_contact_author_address
;
      Universit\'e de Montr\'eal
      D\'epartement de Chimie
      C.P. 6128, Succ. Centre-ville
      Montr\'eal, Qu\'ebec
      Canada, H3C 3J7
;
_publ_contact_author_email       helene.lebel@umontreal.ca
_publ_contact_author_fax         '+1 514 343 2177'
_publ_contact_author_name        'Dr H\'el\`ene Lebel'
_publ_contact_author_phone       '+1 514 343-5826'
_publ_section_title
;
 N-Tosyloxycarbamates as a Source of Metal Nitrenes: Rhodium-Catalyzed C-H
 Insertion and Aziridination Reactions
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14198
_journal_page_last               14199
_journal_paper_doi               10.1021/ja0552850
_journal_volume                  127
_journal_year                    2005
_chemical_absolute_configuration rmad
_chemical_compound_source        'Synthesized by the authors. See text'
_chemical_formula_moiety         'C12 H17 N O2'
_chemical_formula_sum            'C12 H17 N O2'
_chemical_formula_weight         207.27
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.441(2)
_cell_length_b                   11.113(3)
_cell_length_c                   11.410(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      20.00
_cell_volume                     1070.3(5)
_computing_cell_refinement       'CAD4 Program (Nonius 1989)'
_computing_data_collection       'CAD4 Program (Nonius 1989)'
_computing_data_reduction        'Local Program'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  'UdMX (local program)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  Enraf-Nonius-CAD4
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Sealed Tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.031
_diffrn_reflns_av_sigmaI/netI    0.0243
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            15505
_diffrn_reflns_theta_full        69.97
_diffrn_reflns_theta_max         69.97
_diffrn_reflns_theta_min         5.56
_diffrn_standards_decay_%        1.80
_diffrn_standards_interval_time  60
_diffrn_standards_number         5
_exptl_absorpt_coefficient_mu    0.699
_exptl_absorpt_correction_T_max  0.8800
_exptl_absorpt_correction_T_min  0.7200
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'Integration from crystal shape''
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.120
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 'Flack H D (1983), 839 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.1(3)
_refine_ls_extinction_coef       0.052(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   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         2027
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0336
_refine_ls_R_factor_gt           0.0322
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0620P)^2^+0.0061P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0932
_refine_ls_wR_factor_ref         0.0939
_reflns_number_gt                1905
_reflns_number_total             2027
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ja0552850si20050803_052216.cif
_cod_data_source_block           hele10
_cod_database_code               4112027