Iron-Catalyzed Transfer Hydrogenation in Aged <i>N</i>-Methyl-2-pyrrolidone: Reductive Ring-Opening of 3,5-Disubstituted Isoxazoles and Isoxazolines.
Liu, Xiaochen; Hong, Dongsub; Sapir, Netanel G.; Yang, Wen; Hersh, William H.; Leung, Pak-Hing; Yang, Dingqiao; Chen, Yu; The Journal of organic chemistry 84 (2019) 16204–16213; doi:10.1021/acs.joc.9b02733

data_4037627
_publ_section_title
;
 Iron-Catalyzed Transfer Hydrogenation in Aged
 <i>N</i>-Methyl-2-pyrrolidone: Reductive Ring-Opening of
 3,5-Disubstituted Isoxazoles and Isoxazolines.
;
_journal_issue                   24
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              16204
_journal_page_last               16213
_journal_paper_doi               10.1021/acs.joc.9b02733
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C15 H18 O4'
_chemical_formula_sum            'C15 H18 O4'
_chemical_formula_weight         262.29
_chemical_name_systematic
'methyl (Z)-4-(1-hydroxy-4,4-dimethyl-3-oxopent-1-en-1-yl)benzoate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 98.7540(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.1597(5)
_cell_length_b                   21.6415(17)
_cell_length_c                   9.9582(8)
_cell_measurement_reflns_used    9163
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.128
_cell_measurement_theta_min      2.273
_cell_volume                     1312.02(18)
_computing_cell_refinement       'APEX3 v2017.3-0 (Bruker AXS)'
_computing_data_collection       'Bruker Instrument Service v2011.6.0.0'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS, 2017)'
_computing_molecular_graphics    'shelXle (C. B. Huebschle, rev 833)'
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_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Breeze CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0204
_diffrn_reflns_av_unetI/netI     0.0131
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            15047
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.101
_diffrn_reflns_theta_min         1.882
_diffrn_source                   'fine-focus tube'
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2016/2 (Bruker AXS)'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.678
_exptl_crystal_size_mid          0.620
_exptl_crystal_size_min          0.608
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_exptl_transmission_factor_min   0.6982
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_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     180
_refine_ls_number_reflns         2883
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0387
_refine_ls_R_factor_gt           0.0362
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0470P)^2^+0.5575P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0921
_refine_ls_wR_factor_ref         0.0942
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2694
_reflns_number_total             2883
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02733_si_001.cif
_cod_data_source_block           YC_3_XL_22_p338_0m_a
_cod_depositor_comments          'Adding full bibliography for 4037627.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4037627
_shelx_estimated_absorpt_t_min   0.938
_shelx_estimated_absorpt_t_max   0.944
_shelx_res_checksum              7436
_shelx_hkl_checksum              92433