Synthesis of 2-Nitroglycals from Glycals Using the Tetrabutylammonium Nitrate-Trifluoroacetic Anhydride-Triethylamine Reagent System and Base-Catalyzed Ferrier Rearrangement of Acetylated 2-Nitroglycals
Suresh Dharuman; Preeti Gupta; Pavan K. Kancharla; Yashwant D. Vankar; Journal of Organic Chemistry 78 (2013) 8442–8450; doi:10.1021/jo401165y

data_4028530
_publ_section_title
;
 Synthesis of 2-Nitroglycals from Glycals Using the Tetrabutylammonium
 Nitrate-Trifluoroacetic Anhydride-Triethylamine Reagent System and
 Base-Catalyzed Ferrier Rearrangement of Acetylated 2-Nitroglycals
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8442
_journal_page_last               8450
_journal_paper_doi               10.1021/jo401165y
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C16 H23 N O8'
_chemical_formula_weight         357.35
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                84.238(5)
_cell_angle_beta                 83.540(4)
_cell_angle_gamma                78.233(5)
_cell_formula_units_Z            1
_cell_length_a                   5.4454(15)
_cell_length_b                   8.372(2)
_cell_length_c                   9.793(3)
_cell_measurement_reflns_used    1057
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.88
_cell_measurement_theta_min      2.49
_cell_volume                     432.9(2)
_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      100(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0163
_diffrn_reflns_av_sigmaI/netI    0.0405
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            2852
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.30
_diffrn_reflns_theta_min         2.10
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.705647
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_description       block
_exptl_crystal_F_000             190
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.393
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.093
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.1(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         2388
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.110
_refine_ls_R_factor_all          0.0687
_refine_ls_R_factor_gt           0.0507
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0305P)^2^+0.7973P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1065
_refine_ls_wR_factor_ref         0.1438
_reflns_number_gt                2104
_reflns_number_total             2388
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo401165y_si_001.cif
_cod_data_source_block           8mayam
_cod_original_formula_sum        'C16 H23 N1 O8'
_cod_database_code               4028530