trans-(\±)-2-tert-Butyl-3-phenyloxaziridine: A Unique Reagent for the Oxidation of Thiolates into Sulfenates
Cédric Boudou; Matthieu Bergès; Charlène Sagnes; Jana Sopková-de Oliveira Santos; Stéphane Perrio; Patrick Metzner; Journal of Organic Chemistry 72 (2007) 5403–5406; doi:10.1021/jo070700n

data_4024010
_publ_contact_author_address
;     Laboratoire de Chimie Mol\'eculaire et Thioorganique, UMR CNRS 6507 
      Ecole Nationale Sup\'erieure d'Ing\'enieur de Caen - ENSICAEN 
      Universit\'e de Caen 
      6 boulevard du Mar\'echal Juin 
      14050 Caen
      France
;
_publ_contact_author_email       stephane.perrio@ensicaen.fr
_publ_contact_author_fax         '332 31 45 28 77'
_publ_contact_author_name        'Perrio, St\'ephane'
_publ_contact_author_phone       '332 31 45 28 84'
_publ_section_title
;
 trans-(\+-)-2-tert-Butyl-3-phenyloxaziridine: A Unique Reagent
 for the Oxidation of Thiolates into Sulfenates
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5403
_journal_page_last               5406
_journal_paper_doi               10.1021/jo070700n
_journal_volume                  72
_journal_year                    2007
_chemical_absolute_configuration ad
_chemical_compound_source        synthetised
_chemical_formula_moiety         'C18 H22 N O2 P'
_chemical_formula_sum            'C18 H22 N O2 P'
_chemical_formula_weight         315.34
_chemical_melting_point          380.15
_chemical_name_systematic
;
 (+-)-trans-3-t-Butyl-3-methyl-2-(diphenylphosphinoyl)oxaziridine
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.6281(7)
_cell_length_b                   15.8244(14)
_cell_length_c                   8.7576(7)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      18
_cell_volume                     1750.0(2)
_computing_cell_refinement       CAD4/PC
_computing_data_collection       CAD4/PC
_computing_data_reduction        'JANA98 (Pet\<r\'i\<cek & Du\<sek, 1998 )'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf-Nonius CAD4'
_diffrn_measurement_method       \q/2\q
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0264
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5092
_diffrn_reflns_theta_full        29.97
_diffrn_reflns_theta_max         29.97
_diffrn_reflns_theta_min         2.06
_diffrn_standards_decay_%        7.7
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.163
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'translucent dark white'
_exptl_crystal_density_diffrn    1.197
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.36
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 'Flack (1983), 2390 Friedel pairs'
_refine_ls_abs_structure_Flack   0.00(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         5092
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0883
_refine_ls_R_factor_gt           0.0470
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0670P)^2^+0.1742P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1135
_refine_ls_wR_factor_ref         0.1311
_reflns_number_gt                3507
_reflns_number_total             5092
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo070700nsi20070405_120702.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'None' changed to
'none' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_chemical_melting_point' value '107\%' was changed to '380.15' - it
was converted from degrees Celsius(C) to Kelvins(K).

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               4024010