Alkene Dioxygenation with Malonoyl Peroxides: Synthesis of γ-Lactones, Isobenzofuranones, and Tetrahydrofurans.
Alamillo-Ferrer, Carla; Karabourniotis-Sotti, Marianna; Kennedy, Alan R.; Campbell, Matthew; Tomkinson, Nicholas C. O.; Organic letters 18 (2016) 3102–3105; doi:10.1021/acs.orglett.6b01253

data_1543802
_publ_section_title
;
 Alkene Dioxygenation with Malonoyl Peroxides: Synthesis of \g-Lactones,
 Isobenzofuranones, and Tetrahydrofurans.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              3102
_journal_page_last               3105
_journal_paper_doi               10.1021/acs.orglett.6b01253
_journal_volume                  18
_journal_year                    2016
_chemical_formula_sum            'C15 H13 Br O6'
_chemical_formula_weight         369.16
_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                 98.725(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.5589(5)
_cell_length_b                   5.3450(2)
_cell_length_c                   18.6931(8)
_cell_measurement_reflns_used    3448
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      29.2060
_cell_measurement_theta_min      4.0460
_cell_volume                     1437.81(10)
_computing_cell_refinement       CrysalisPro
_computing_data_collection       CrysalisPro
_computing_data_reduction        CrysalisPro
_computing_publication_material  SHELXL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    SHELXS
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measurement_device_type  'Oxford Diffraction Gemini S'
_diffrn_measurement_method       '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  0.0374
_diffrn_reflns_av_sigmaI/netI    0.0379
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            12579
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         28.99
_diffrn_reflns_theta_min         2.79
_exptl_absorpt_coefficient_mu    2.886
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54610
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.705
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       slab
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.449
_refine_diff_density_min         -0.482
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         3605
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0336
_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^)+(0.0300P)^2^+0.4980P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0684
_refine_ls_wR_factor_ref         0.0736
_reflns_number_gt                2980
_reflns_number_total             3605
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ol6b01253_si_002.cif
_cod_data_source_block           tom_caf_564a
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               1543802