Mechanistic and Synthetic Implications of the Diol-Ritter Reaction: Unexpected Yet Reversible Pathways in the Regioselective Synthesis of Vicinal-Aminoalcohols.
Ondari, Mark E.; Klosin, Jerzy; Froese, Robert D. J.; Kruper, William R.; MacDonald, Jason; Arriola, Dan J.; Bell, Bruce M.; Briggs, John R.; Kruper, William J.; The Journal of organic chemistry 84 (2019) 4715–4722; doi:10.1021/acs.joc.8b02320

data_4035933
_publ_section_title
;
 Mechanistic and Synthetic Implications of the Diol-Ritter Reaction:
 Unexpected Yet Reversible Pathways in the Regioselective Synthesis of
 Vicinal-Aminoalcohols.
;
_journal_issue                   8
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4715
_journal_page_last               4722
_journal_paper_doi               10.1021/acs.joc.8b02320
_journal_volume                  84
_journal_year                    2019
_chemical_formula_sum            'C11 H14 Cl6 N O3 Sb'
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_atom_sites_solution_hydrogens   mixed
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_diffrn_ambient_temperature      100(2)
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_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
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_diffrn_reflns_Laue_measured_fraction_full 1.000
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_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
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_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
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_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
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_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_min         2.100
_exptl_absorpt_coefficient_mu    2.336
_exptl_absorpt_correction_T_max  0.66
_exptl_absorpt_correction_T_min  0.45
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
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_exptl_crystal_description       block
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.572
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    mixed
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_refine_ls_number_reflns         4308
_refine_ls_number_restraints     0
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_refine_ls_R_factor_all          0.0186
_refine_ls_R_factor_gt           0.0175
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0165P)^2^+1.2703P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0418
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_reflns_number_gt                4119
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_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02320_si_004.cif
_cod_data_source_block           Final
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4035933
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_shelx_res_checksum              26760
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