Synthesis of Highly Substituted 2,3-Dihydro-1H-pyrrole Derivatives via a Tandem Regioselective Addition of Nitrones to 1,3-Enynes with Subsequent Rearrangement
Sivaperuman Saravanan; Ismail Abulkalam Azath; Shanmugam Muthusubramanian; Journal of Organic Chemistry 73 (2008) 2323–2329; doi:10.1021/jo702610j

data_4023344
_publ_contact_author_address
;
Department of Organic Chemistry
School of Chemistry
Madurai Kamaraj University
Madurai 625 021
India
;
_publ_contact_author_email       muthumanian2001@yahoo.com
_publ_contact_author_name        'Prof.Shanmugam Muthusubramanian'
_publ_contact_author_phone       '0452 2458246'
_publ_section_title
;
 Synthesis of Highly Substituted 2,3-Dihydro-1H-pyrrole Derivatives
 via a Tandem Regioselective Addition of Nitrones to 1,3-Enynes
 with Subsequent Rearrangement
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2323
_journal_page_last               2329
_journal_paper_doi               10.1021/jo702610j
_journal_volume                  73
_journal_year                    2008
_chemical_formula_moiety         'C20 H14 Cl N3 O2 Se'
_chemical_formula_sum            'C20 H14 Cl N3 O2 Se'
_chemical_formula_weight         442.75
_chemical_melting_point          127
_chemical_name_systematic
;
Ethyl (Z)-3-(4-chlorophenyl)-2-cyano-3-(4-phenyl-1,2,3-selenadiazol-5-yl)-
  2-propenoate

;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             '20 September 2006'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 102.643(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   22.158(8)
_cell_length_b                   12.990(5)
_cell_length_c                   13.502(7)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      14.21
_cell_measurement_theta_min      10.26
_cell_volume                     3792(2)
_computing_cell_refinement       'CAD4 Express'
_computing_data_collection       'CAD4 Express (Enraf Nonius, (1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'MACH3-Nonius sealed tube'
_diffrn_measurement_method       \w-2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_sigmaI/netI    0.0489
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3738
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.26
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    2.141
_exptl_absorpt_correction_T_max  0.9957
_exptl_absorpt_correction_T_min  0.9871
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   'North et al., 1968'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.551
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             1776
_exptl_crystal_preparation       Ethanol
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.442
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3328
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0924
_refine_ls_R_factor_gt           0.0375
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0545P)^2^+1.5640P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0864
_refine_ls_wR_factor_ref         0.1041
_reflns_number_gt                2027
_reflns_number_total             3328
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            jo702610j-File004.cif
_cod_data_source_block           etcn
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4023344