Thermal C^2^-C^6^ Cyclization of Enyne-Allenes. Experimental Evidence for a Stepwise Mechanism and for an Unusual Thermal Silyl Shift
Michael Schmittel; Atul A. Mahajan; Götz Bucher; Jan W. Bats; Journal of Organic Chemistry 72 (2007) 2166–2173; doi:10.1021/jo062448+

data_4022797
_publ_section_title
;
 Thermal C^2^-C^6^ Cyclization of Enyne-Allenes. Experimental Evidence
 for a Stepwise Mechanism and for an Unusual Thermal Silyl Shift
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2166
_journal_page_last               2173
_journal_paper_doi               10.1021/jo062448+
_journal_volume                  72
_journal_year                    2007
_chemical_formula_moiety         'C17 H14'
_chemical_formula_sum            'C17 H14'
_chemical_formula_weight         218.28
_chemical_name_systematic
; 
1-(2-ethynyl-1-phenylcyclopropyl)benzene
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.262(2)
_cell_length_b                   10.0367(14)
_cell_length_c                   7.5255(9)
_cell_measurement_reflns_used    174
_cell_measurement_temperature    158(2)
_cell_measurement_theta_max      23
_cell_measurement_theta_min      3
_cell_volume                     1228.3(3)
_computing_cell_refinement       'SMART (Siemens, 1995)'
_computing_data_collection       'SMART (Siemens, 1995)'
_computing_data_reduction        'SAINT (Siemens, 1995)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      158(2)
_diffrn_measured_fraction_theta_full 0.947
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measurement_device_type  SIEMENS_SMART_CCD
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0629
_diffrn_reflns_av_sigmaI/netI    0.0299
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            18984
_diffrn_reflns_theta_full        30.92
_diffrn_reflns_theta_max         30.92
_diffrn_reflns_theta_min         2.38
_diffrn_standards_decay_%        0.0
_diffrn_standards_interval_time  1200
_diffrn_standards_number         235
_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.180
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.135
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     170
_refine_ls_number_reflns         1965
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.135
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0423
_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^)+(0.05P)^2^+0.1P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0913
_refine_ls_wR_factor_ref         0.0989
_reflns_number_gt                1657
_reflns_number_total             1965
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            jo062448+si20061129_012539.cif
_cod_data_source_block           compound_17
_cod_database_code               4022797