Reactions of Conjugate Phosphinyl- and Phosphonyl-Nitroso Alkenes with Enamines. Preparation of N-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_4024518
_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, Jes\'us M.'
_publ_section_title
;
Reactions of Conjugate Phosphinyl- and Phosphonyl-Nitroso Alkenes with
Enamines. Preparation of N-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         'C14 H24 N O4 P'
_chemical_formula_sum            'C14 H24 N O4 P'
_chemical_formula_weight         301.31
_chemical_name_systematic
; 
 Diethyl 1-hydroxy-2,5-dimethyl-4,5,6,7-tetrahydro-1H-indol-3-ylphosphonate
;
_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                 99.279(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.3987(19)
_cell_length_b                   8.8054(9)
_cell_length_c                   15.3697(25)
_cell_measurement_reflns_used    9130
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.27
_cell_measurement_theta_min      1.96
_cell_volume                     1656.1(4)
_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 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details      ' 180 frames, detector distance = 100 mm'
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_collimation    '0.5 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  0.0686
_diffrn_reflns_av_sigmaI/netI    0.0906
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            12997
_diffrn_reflns_theta_full        29.20
_diffrn_reflns_theta_max         29.20
_diffrn_reflns_theta_min         1.96
_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
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.178
_exptl_absorpt_correction_T_max  0.9777
_exptl_absorpt_correction_T_min  0.9201
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'X-RED (Stoe & Cie, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.209
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             648
_refine_diff_density_max         0.589
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         4379
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.121
_refine_ls_R_factor_all          0.2010
_refine_ls_R_factor_gt           0.0895
_refine_ls_shift/su_max          0.050
_refine_ls_shift/su_mean         0.026
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'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          0.2158
_refine_ls_wR_factor_ref         0.2548
_reflns_number_gt                1760
_reflns_number_total             4379
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo900489j_si_003.cif
_cod_data_source_block           ro1
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               4024518