The aza-wharton reaction: syntheses of cyclic allylic amines and vicinal hydroxyamines from the respective acylaziridines.
Silva, Saúl; Rodrigues, Paula; Bento, Isabel; Maycock, Christopher D.; The Journal of organic chemistry 80 (2015) 3067–3074; doi:10.1021/jo5029387

data_4030768
_publ_section_title
;
 The aza-wharton reaction: syntheses of cyclic allylic amines and vicinal
 hydroxyamines from the respective acylaziridines.
;
_journal_issue                   6
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3067
_journal_page_last               3074
_journal_paper_doi               10.1021/jo5029387
_journal_volume                  80
_journal_year                    2015
_chemical_formula_sum            'C13 H15 N O'
_chemical_formula_weight         201.26
_space_group_IT_number           4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 105.678(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.1102(14)
_cell_length_b                   5.2791(9)
_cell_length_c                   13.309(2)
_cell_measurement_temperature    296(2)
_cell_volume                     548.62(16)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0198
_diffrn_reflns_av_sigmaI/netI    0.0312
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6471
_diffrn_reflns_theta_full        31.51
_diffrn_reflns_theta_max         31.51
_diffrn_reflns_theta_min         1.59
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.9699
_exptl_absorpt_correction_T_min  0.9000
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             216
_exptl_crystal_size_max          1.40
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         3384
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0385
_refine_ls_shift/su_max          1.626
_refine_ls_shift/su_mean         0.047
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0606P)^2^+0.0616P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0976
_refine_ls_wR_factor_ref         0.1017
_reflns_number_gt                3071
_reflns_number_total             3384
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5029387_si_002.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
'Adding full bibliography for 4030767--4030768.cif.'
_cod_original_cell_volume        548.60(16)
_cod_database_code               4030768