Oxidative Difunctionalization of 2-Amino-4H-pyrans in Iodobenzene Diacetate and N-Chlorosuccinimide: Reactivity, Mechanistic Insights, and DFT Calculations
Santhosh Reddy Mandha; Manjula Alla; Vittal Rao Bommena; Jagadeesh Babu Nanubolu; Santosh Kumar Lingala; Soujanya Yarasi; Journal of Organic Chemistry 77 (2012) 10648–10654; doi:10.1021/jo301801b

data_4027755
_publ_section_title
;
 Oxidative Difunctionalization of 2-Amino-4H-pyrans in Iodobenzene
 Diacetate and N-Chlorosuccinimide: Reactivity, Mechanistic Insights, and
 DFT Calculations
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              10648
_journal_page_last               10654
_journal_paper_doi               10.1021/jo301801b
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C22 H18 Cl2 N2 O2'
_chemical_formula_sum            'C22 H18 Cl2 N2 O2'
_chemical_formula_weight         413.28
_chemical_name_systematic
;
2-amino-3-chloro-2-ethoxy-4-phenyl-
3,4-dihydro-2H-benzo[h]chromene-3-carbonitrile
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 99.8140(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.8794(5)
_cell_length_b                   10.5049(5)
_cell_length_c                   17.5593(8)
_cell_measurement_reflns_used    9613
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      27.76
_cell_measurement_theta_min      2.27
_cell_volume                     1977.43(16)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0178
_diffrn_reflns_av_sigmaI/netI    0.0126
_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       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            18509
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.90
_exptl_absorpt_coefficient_mu    0.349
_exptl_absorpt_correction_T_max  0.8731
_exptl_absorpt_correction_T_min  0.7923
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_description       block
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.60
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3477
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0373
_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^)+(0.0543P)^2^+0.6317P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1026
_refine_ls_wR_factor_ref         0.1056
_reflns_number_gt                3142
_reflns_number_total             3477
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo301801b_si_002_3.cif
_cod_data_source_block           6g
_cod_original_sg_symbol_H-M      'P 1 21/c 1 '
_cod_database_code               4027755