Practical Procedures for the Preparation of N-tert-Butyldimethylsilylhydrazones and Their Use in Modified Wolff-Kishner Reductions and in the Synthesis of Vinyl Halides and gem-Dihalides
Michael E. Furrow; Andrew G. Myers; Journal of the American Chemical Society 126 (2004) 5436–5445; doi:10.1021/ja049694s

data_4112541
_publ_section_title
;
 Practical Procedures for the Preparation of
 N-tert-Butyldimethylsilylhydrazones and Their Use in Modified
 Wolff-Kishner Reductions and in the Synthesis of Vinyl Halides and
 gem-Dihalides
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5436
_journal_page_last               5445
_journal_paper_doi               10.1021/ja049694s
_journal_volume                  126
_journal_year                    2004
_chemical_formula_moiety         'C14 H24 N2 Si'
_chemical_formula_sum            'C14 H24 N2 Si'
_chemical_formula_weight         248.44
_chemical_name_common
'para-tolualdehyde N-tert-butyldimethylsilylhydrozone'
_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                 93.928(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.8315(15)
_cell_length_b                   7.4154(16)
_cell_length_c                   30.720(7)
_cell_measurement_temperature    193(2)
_cell_volume                     1552.6(6)
_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      193(2)
_diffrn_detector_area_resol_mean 836.6
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0810
_diffrn_reflns_av_sigmaI/netI    0.1178
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            10734
_diffrn_reflns_theta_full        28.30
_diffrn_reflns_theta_max         28.30
_diffrn_reflns_theta_min         1.33
_exptl_absorpt_coefficient_mu    0.135
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.063
_exptl_crystal_density_meas      0
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.393
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         3843
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.990
_refine_ls_R_factor_all          0.1493
_refine_ls_R_factor_gt           0.0766
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0526P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1284
_refine_ls_wR_factor_ref         0.1475
_reflns_number_gt                2044
_reflns_number_total             3843
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja049694ssi20040116_064627.cif
_cod_data_source_block           amh49t
_cod_database_code               4112541