Regioselective transformation of O-propargylic arylaldoximes to four-membered cyclic nitrones by copper-catalyzed skeletal rearrangement.
Nakamura, Itaru; Araki, Toshiharu; Zhang, Dong; Kudo, Yu; Kwon, Eunsang; Terada, Masahiro; Organic letters 13 (2011) 3616–3619; doi:10.1021/ol2012583

data_1502274
_publ_section_title
;
 Regioselective transformation of O-propargylic arylaldoximes to
 four-membered cyclic nitrones by copper-catalyzed skeletal rearrangement.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              3616
_journal_page_last               3619
_journal_paper_doi               10.1021/ol2012583
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety         'C24 H18 F3 N O2'
_chemical_formula_sum            'C24 H18 F3 N O2'
_chemical_formula_weight         409.41
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                79.398(11)
_cell_angle_beta                 80.237(11)
_cell_angle_gamma                79.763(12)
_cell_formula_units_Z            4
_cell_length_a                   9.800(4)
_cell_length_b                   9.819(4)
_cell_length_c                   21.005(8)
_cell_measurement_reflns_used    4903
_cell_measurement_temperature    150
_cell_measurement_theta_max      27.44
_cell_measurement_theta_min      3.03
_cell_volume                     1935.4(13)
_computing_cell_refinement       CrystalClear
_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_data_reduction        CrystalClear
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 7.314
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Rigaku Saturn70'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            28460
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.974
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             848.00
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.570
_refine_diff_density_min         -0.510
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     541
_refine_ls_number_reflns         8737
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0603
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0940P)^2^+0.5827P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1783
_reflns_number_gt                6896
_reflns_number_total             8737
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            ol2012583_si_001.cif
_cod_data_source_block           a
_cod_original_cell_volume        1935.3(12)
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