An Unexpectedly Mild Thermal Alder-Ene-Type Cyclization of Enallenes
Katja Närhi; Johan Franzén; Jan-E. Bäckvall; Journal of Organic Chemistry 71 (2006) 2914–2917; doi:10.1021/jo060013g

data_4021619
_publ_section_title
;
 An Unexpectedly Mild Thermal Alder-Ene-Type Cyclization of Enallenes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2914
_journal_page_last               2917
_journal_paper_doi               10.1021/jo060013g
_journal_volume                  71
_journal_year                    2006
_chemical_formula_moiety         'C20 H24 O7'
_chemical_formula_sum            'C40 H48 O14'
_chemical_formula_weight         752.78
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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                102.64(4)
_cell_angle_beta                 103.02(4)
_cell_angle_gamma                110.17(4)
_cell_formula_units_Z            2
_cell_length_a                   10.356(4)
_cell_length_b                   14.180(6)
_cell_length_c                   14.807(5)
_cell_measurement_reflns_used    5000
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.0
_cell_measurement_theta_min      2.55
_cell_volume                     1880.9(12)
_computing_cell_refinement       'Cell (STOE, 1997)'
_computing_data_collection       'Expose (STOE, 1997)'
_computing_data_reduction        'Integrate (STOE, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 6.0
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  'STOE IPDS'
_diffrn_measurement_method       'Area detector \f scan'
_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  0.1697
_diffrn_reflns_av_sigmaI/netI    0.1090
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            36643
_diffrn_reflns_theta_full        28.34
_diffrn_reflns_theta_max         28.34
_diffrn_reflns_theta_min         2.53
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.026(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.957
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     488
_refine_ls_number_reflns         9054
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.957
_refine_ls_R_factor_all          0.0926
_refine_ls_R_factor_gt           0.0519
_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^)+(0.0726P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1370
_refine_ls_wR_factor_ref         0.1573
_reflns_number_gt                5164
_reflns_number_total             9054
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo060013gsi20060104_083056.cif
_cod_database_code               4021619