Reactions of Conjugate Phosphinyl- and Phosphonyl-Nitroso Alkenes with Enamines. Preparation ofN-Hydroxypyrrole Derivatives
Jesús M. de los Santos; Roberto Ignacio; Domitila Aparicio; Francisco Palacios; José M. Ezpeleta; Journal of Organic Chemistry 74 (2009) 3444–3448; doi:10.1021/jo900489j

data_4024519
_publ_contact_author_address
;
Departamento de Qu\'imica Org\'anica
Facultad de Farmacia 
Universidad del Pa\'is Vasco
Apdo. 450
01080 Vitoria
Spain
;
_publ_contact_author_email       jesus.delossantos@ehu.es
_publ_contact_author_name        'de los Santos, Jesus M.'
_publ_section_title
;
Reactions of Conjugate Phosphinyl- and Phosphonyl-Nitroso Alkenes with
Enamines. Preparation ofN-Hydroxypyrrole Derivatives
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3444
_journal_page_last               3448
_journal_paper_doi               10.1021/jo900489j
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         'C20 H22 N O2 P'
_chemical_formula_sum            'C20 H22 N O2 P'
_chemical_formula_weight         339.36
_chemical_name_systematic
; 
 3-(Diphenylphosphoryl)-4-isopropyl-2-methyl-1H-pyrrol-1-ol
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 103.872(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.8044(8)
_cell_length_b                   9.0310(5)
_cell_length_c                   20.3865(18)
_cell_measurement_reflns_used    4411
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.83
_cell_measurement_theta_min      2.06
_cell_volume                     1752.45(22)
_computing_cell_refinement       'STOE X-AREA (Stoe & Cie, 2002)'
_computing_data_collection       'STOE X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'STOE X-RED (Stoe & Cie, 2002)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution
;
SIR97 (Altomare, Cascaramo, Giacovazzo, Guagliardi, Molitemi, Burla,
Polidori, Camalli & Spagna, 1997)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
; 174 frames, detector distance = 80 mm
    Reference Run
      Phi                  : 54.0
      Omega range          : 6.0 - 16.0
      Omega increment      : 10.0
      Exposure time [min]  : 2.0
      Frames               : 1
      Interval [h]         : 1.00

    Run #1
      Phi                  : 54.0
      Omega range          : 6.0 - 180.0
      Omega increment      : 1.0
      Exposure time [min]  : 3.0
      Frames               : 174

    Measured runs                        : 1 (out of 1)
    Measured frames                      : 174 (out of 174)
    Remeasured frames with filter        : 0
    Measured reference runs              : 14
    Statistics over all measured frames
      Mean minimum pixel intensity       : 1.0
      Mean average pixel intensity       : 11.2
      Mean maximum pixel intensity       : 4993.9
      Total number of overflow pixels    : 0

;
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_collimation    '0.8 mm diameter, monocapillary'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0580
_diffrn_reflns_av_sigmaI/netI    0.0934
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            10494
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.06
_diffrn_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_source_current           40
_diffrn_source_power             2.00
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.169
_exptl_absorpt_correction_T_max  0.9910
_exptl_absorpt_correction_T_min  0.9440
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'X-RED (Stoe & Cie, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.612
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3091
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.612
_refine_ls_R_factor_all          0.0873
_refine_ls_R_factor_gt           0.0410
_refine_ls_shift/su_max          0.050
_refine_ls_shift/su_mean         0.023
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0974
_refine_ls_wR_factor_ref         0.1176
_reflns_number_gt                1809
_reflns_number_total             3091
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo900489j_si_004.cif
_cod_data_source_block           ro2
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               4024519