Acid-catalyzed regioselective sulfetherification of alkenols and stereoselective rearrangement of tetrahydrofuran to tetrahydropyran.
Wang, Haining; Huang, Deshun; Cheng, Donghao; Li, Lijun; Shi, Yian; Organic letters 13 (2011) 1650–1653; doi:10.1021/ol200127n

data_1502041
_publ_section_title
;
 Acid-catalyzed regioselective sulfetherification of alkenols and
 stereoselective rearrangement of tetrahydrofuran to tetrahydropyran.
;
_journal_issue                   7
_journal_name_full               'Organic letters'
_journal_page_first              1650
_journal_page_last               1653
_journal_paper_doi               10.1021/ol200127n
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety         'C19 H21 Br O S'
_chemical_formula_sum            'C19 H21 Br O S'
_chemical_formula_weight         377.33
_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                109.340(10)
_cell_angle_beta                 93.580(11)
_cell_angle_gamma                101.960(12)
_cell_formula_units_Z            2
_cell_length_a                   5.7147(13)
_cell_length_b                   11.254(2)
_cell_length_c                   14.617(3)
_cell_measurement_reflns_used    435
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.17
_cell_volume                     859.0(3)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics    'XP in Siemens SHELXTL (Sheldrick, 1994)'
_computing_publication_material  'SHELX97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_sigmaI/netI    0.0415
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11480
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.87
_exptl_absorpt_coefficient_mu    2.514
_exptl_absorpt_correction_T_max  0.6333
_exptl_absorpt_correction_T_min  0.5293
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.415
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3931
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0430
_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^)+(0.0228P)^2^+0.6615P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0828
_refine_ls_wR_factor_ref         0.0854
_reflns_number_gt                3584
_reflns_number_total             3931
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol200127n_si_002.cif
_cod_data_source_block           a
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1502041