Silver- and Gold-Catalyzed Intramolecular Rearrangement of Propargylic Alcohols Tethered with Methylenecyclopropanes: Stereoselective Synthesis of Allenylcyclobutanols and 1-Vinyl-3-oxabicyclo[3.2.1]octan-8-one Derivatives
Liang-Feng Yao; Yin Wei; Min Shi; Journal of Organic Chemistry 74 (2009) 9466–9469; doi:10.1021/jo902261r

data_4025119
_publ_section_title
;
Silver- and Gold-Catalyzed Intramolecular Rearrangement of Propargylic
Alcohols Tethered with Methylenecyclopropanes: Stereoselective Synthesis of
Allenylcyclobutanols and 1-Vinyl-3-oxabicyclo[3.2.1]octan-8-one Derivatives
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_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9466
_journal_page_last               9469
_journal_paper_doi               10.1021/jo902261r
_journal_volume                  74
_journal_year                    2009
_chemical_formula_sum            'C28 H26 O3'
_chemical_formula_weight         410.49
_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                 108.179(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.5410(18)
_cell_length_b                   16.611(2)
_cell_length_c                   10.4723(14)
_cell_measurement_reflns_used    962
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      36.908
_cell_measurement_theta_min      4.772
_cell_volume                     2237.9(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and 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  0.1409
_diffrn_reflns_av_sigmaI/netI    0.1694
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11956
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         2.00
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75149
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.217
_exptl_crystal_size_mid          0.216
_exptl_crystal_size_min          0.041
_refine_diff_density_max         0.136
_refine_diff_density_min         -0.146
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.868
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         4382
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.868
_refine_ls_R_factor_all          0.1310
_refine_ls_R_factor_gt           0.0474
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
; calc 
 [0.00000+1.00000exp(3.00(sin\q/\l)^2^)]/ 
   [\s^2^(Fo^2^)+0.0000+0.0000*P+(0.0000P)^2^+0.0000sin\q/\l] 
 where P = 0.33333Fo^2^ + 0.66667Fc^2^ 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0913
_refine_ls_wR_factor_ref         0.1176
_reflns_number_gt                1745
_reflns_number_total             4382
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo902261r_si_002.cif
_cod_data_source_block           cd29237
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
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_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4025119