Brønsted Acid-Catalyzed Cycloisomerization of But-2-yne-1,4-diols with or without 1,3-Dicarbonyl Compounds to Tri- and Tetrasubstituted Furans
Srinivasa Reddy Mothe; Sherman Jun Liang Lauw; Prasath Kothandaraman; Philip Wai Hong Chan; Journal of Organic Chemistry 77 (2012) 6937–6947; doi:10.1021/jo301093f

data_4027385
_publ_section_title
;
 Br\/onsted Acid-Catalyzed Cycloisomerization of But-2-yne-1,4-diols with
 or without 1,3-Dicarbonyl Compounds to Tri- and Tetrasubstituted Furans
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6937
_journal_page_last               6947
_journal_paper_doi               10.1021/jo301093f
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C37 H24 Br2 O2'
_chemical_formula_sum            'C37 H24 Br2 O2'
_chemical_formula_weight         660.38
_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                80.949(3)
_cell_angle_beta                 86.310(2)
_cell_angle_gamma                78.412(2)
_cell_formula_units_Z            2
_cell_length_a                   6.0736(2)
_cell_length_b                   9.8371(4)
_cell_length_c                   24.1530(11)
_cell_measurement_reflns_used    3980
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      26.27
_cell_measurement_theta_min      2.42
_cell_volume                     1395.24(10)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      103(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w 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  0.0598
_diffrn_reflns_av_sigmaI/netI    0.0755
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            24653
_diffrn_reflns_theta_full        28.39
_diffrn_reflns_theta_max         28.39
_diffrn_reflns_theta_min         1.71
_exptl_absorpt_coefficient_mu    2.939
_exptl_absorpt_correction_T_max  0.9436
_exptl_absorpt_correction_T_min  0.5910
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.572
_exptl_crystal_description       needle
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.519
_refine_diff_density_min         -0.518
_refine_diff_density_rms         0.115
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     370
_refine_ls_number_reflns         6934
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0773
_refine_ls_R_factor_gt           0.0393
_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^)+(0.0173P)^2^+2.3342P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0663
_refine_ls_wR_factor_ref         0.0900
_reflns_number_gt                4766
_reflns_number_total             6934
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo301093f_si_001.cif
_cod_data_source_block           chan164
_cod_database_code               4027385