Highly selective synthesis of tetra-substituted furans and cyclopropenes: copper(i)-catalyzed formal cycloadditions of internal aryl alkynes and diazoacetates.
Swenson, Andrew K.; Higgins, Kate E.; Brewer, Matthew G.; Brennessel, William W.; Coleman, Michael G.; Organic & biomolecular chemistry 10 (2012) 7483–7486; doi:10.1039/c2ob26295a

data_7152607
_publ_section_title
;
 Highly selective synthesis of tetra-substituted furans and cyclopropenes:
 copper(i)-catalyzed formal cycloadditions of internal aryl alkynes and
 diazoacetates.
;
_journal_issue                   37
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7483
_journal_page_last               7486
_journal_paper_doi               10.1039/c2ob26295a
_journal_volume                  10
_journal_year                    2012
_chemical_formula_moiety         'C15 H16 O4'
_chemical_formula_sum            'C15 H16 O4'
_chemical_formula_weight         260.28
_chemical_name_common            ritmc01
_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                 100.477(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.1969(10)
_cell_length_b                   11.1313(12)
_cell_length_c                   12.8767(14)
_cell_measurement_reflns_used    3958
_cell_measurement_temperature    100.0(5)
_cell_measurement_theta_max      37.83
_cell_measurement_theta_min      2.25
_cell_volume                     1296.3(2)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2011)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      100.0(5)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD Platform'
_diffrn_measurement_method       'area detector, \w scans per \f'
_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  0.0378
_diffrn_reflns_av_sigmaI/netI    0.0237
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            46703
_diffrn_reflns_theta_full        37.78
_diffrn_reflns_theta_max         37.78
_diffrn_reflns_theta_min         2.25
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.9716
_exptl_absorpt_correction_T_min  0.9579
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.641
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         6902
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0417
_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^)+(0.0716P)^2^+0.1872P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1139
_refine_ls_wR_factor_ref         0.1247
_reflns_number_gt                5431
_reflns_number_total             6902
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ob26295a.txt
_cod_data_source_block           ritmc01
_cod_database_code               7152607