Iodine(III)-promoted ring expansion of 1-vinylcycloalkanol derivatives: a metal-free approach toward seven-membered rings.
Silva, Jr, Luiz F; Vasconcelos, Ramon S.; Nogueira, Mário A; Organic letters 10 (2008) 1017–1020; doi:10.1021/ol800048f

data_1504569
_publ_section_title
;
 Iodine(III)-promoted ring expansion of 1-vinylcycloalkanol derivatives: a
 metal-free approach toward seven-membered rings.
;
_journal_issue                   5
_journal_name_full               'Organic letters'
_journal_page_first              1017
_journal_page_last               1020
_journal_paper_doi               10.1021/ol800048f
_journal_volume                  10
_journal_year                    2008
_chemical_formula_sum            'C24 H24 O2'
_chemical_formula_weight         344.43
_space_group_IT_number           2
_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                78.439(3)
_cell_angle_beta                 74.706(4)
_cell_angle_gamma                78.919(2)
_cell_formula_units_Z            2
_cell_length_a                   7.746(2)
_cell_length_b                   9.390(2)
_cell_length_c                   13.269(10)
_cell_measurement_temperature    293(2)
_cell_volume                     902.1(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0340
_diffrn_reflns_av_sigmaI/netI    0.0753
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3999
_diffrn_reflns_theta_full        26.47
_diffrn_reflns_theta_max         26.47
_diffrn_reflns_theta_min         4.01
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.9883
_exptl_absorpt_correction_T_min  0.9863
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3717
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.1392
_refine_ls_R_factor_gt           0.0516
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0666P)^2^+0.0073P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1115
_refine_ls_wR_factor_ref         0.1426
_reflns_number_gt                1942
_reflns_number_total             3717
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol800048f-file001.cif
_cod_data_source_block           s97
_cod_database_code               1504569