Electrophile-Induced C-C Bond Activation of Vinylcyclopropanes for the Synthesis of Z-Alkylidenetetrahydrofurans
Venkataraman Ganesh; Taraknath Kundu; Srinivasan Chandrasekaran; Journal of Organic Chemistry 78 (2013) 380–399; doi:10.1021/jo302204k

data_4027850
_publ_contact_author_address
;

Department of Organic Chemistry

Indian Institute of Science

Bangaloe 560012, Karnataka

India

;
_publ_contact_author_email       scn@orgchem.iisc.ernet.in
_publ_contact_author_fax         '+91 80 23600529'
_publ_contact_author_name        'Prof. Srinivasan Chandrasekaran'
_publ_contact_author_phone       '+91 80 22932404'
_publ_section_title
;
 Electrophile-Induced C-C Bond Activation of Vinylcyclopropanes for the
 Synthesis of Z-Alkylidenetetrahydrofurans
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              380
_journal_page_last               399
_journal_paper_doi               10.1021/jo302204k
_journal_volume                  78
_journal_year                    2013
_chemical_absolute_configuration Z
_chemical_formula_moiety         'C25 H25 N O3 S'
_chemical_formula_sum            'C25 H25 N O3 S'
_chemical_formula_weight         419.53
_chemical_melting_point          150(2)
_chemical_name_common            'Alkyidene Furan'
_chemical_name_systematic
; 

 (Z)-N-(2-(5,5-diphenyldihydrofuran-3(2H)-ylidene)ethyl)
-4-methylbenzenesulfonamide 

;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 92.913(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.3722(6)
_cell_length_b                   8.8919(4)
_cell_length_c                   20.1596(10)
_cell_measurement_reflns_used    4347
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.0
_cell_measurement_theta_min      1.9
_cell_volume                     2214.94(18)
_computing_cell_refinement       'SMART APEXX II'
_computing_data_collection       'SMART APEX II (Bruker)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics
'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)'
_computing_publication_material  'PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_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  0.0519
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_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            16237
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         1.89
_exptl_absorpt_coefficient_mu    0.172
_exptl_absorpt_correction_T_max  0.9831
_exptl_absorpt_correction_T_min  0.9312
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_description       block
_exptl_crystal_F_000             892
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.959
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         4126
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.959
_refine_ls_R_factor_all          0.1425
_refine_ls_R_factor_gt           0.0564
_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^)+(0.0755P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
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_refine_ls_wR_factor_ref         0.1572
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