Synthesis of 1-hydroperoxy-1′-alkoxyperoxides by the iodine-catalyzed reactions of geminal bishydroperoxides with acetals or enol ethers
Terent'ev, Alexander O.; Platonov, Maxim M.; Krylov, Igor B.; Chernyshev, Vladimir V.; Nikishin, Gennady I.; Organic & Biomolecular Chemistry 6 (2008) 4435–4441; doi:10.1039/b809661a

data_7150998
_publ_section_title
;
 Synthesis of 1-hydroperoxy-1&#x2032;-alkoxyperoxides by the
 iodine-catalyzed reactions of geminal bishydroperoxides with acetals
 or enol ethers
;
_journal_issue                   23
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_page_first              4435
_journal_page_last               4441
_journal_paper_doi               10.1039/b809661a
_journal_volume                  6
_journal_year                    2008
_chemical_formula_moiety         'C19 H36 O5'
_chemical_formula_sum            'C19 H36 O5'
_chemical_formula_weight         344.48
_chemical_name_common
'1-((1-Methoxycyclohexyl)peroxy)cyclododecyl hydroperoxide'
_chemical_name_systematic
;
1-[(1-Methoxycyclohexyl)peroxy]cyclododecyl hydroperoxide
;
_space_group_IT_number           2
_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                109.105(11)
_cell_angle_beta                 95.714(12)
_cell_angle_gamma                93.578(12)
_cell_formula_units_Z            2
_cell_length_a                   8.3859(13)
_cell_length_b                   10.9820(14)
_cell_length_c                   11.3351(16)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      34.45
_cell_measurement_theta_min      28.20
_cell_volume                     976.5(3)
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'scintillation LiI'
_diffrn_detector_dtime           1.195
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       'non-profiled omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_av_sigmaI/netI    0.0945
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3904
_diffrn_reflns_theta_full        70.06
_diffrn_reflns_theta_max         70.06
_diffrn_reflns_theta_min         4.16
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_standards_decay_%        5
_diffrn_standards_interval_count 150
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.666
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.933
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details
;
North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351
Number of psi-scan sets used was 5
Theta correction was applied.
Averaged transmission function was used.
No Fourier smoothing was applied.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.172
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.936
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3703
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.936
_refine_ls_R_factor_all          0.1259
_refine_ls_R_factor_gt           0.0518
_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^)+(0.1081P)^2^+0.1915P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1215
_refine_ls_wR_factor_ref         0.1959
_reflns_number_gt                1685
_reflns_number_total             3703
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b809661a.txt
_cod_data_source_block           ioh1302
_cod_database_code               7150998