Absolute configuration of 3,3'-diphenyl-[2,2'-binaphthalene]-1,1'-diol revisited.

نویسندگان

  • Prasad L Polavarapu
  • Ana G Petrovic
  • Sarah E Vick
  • William D Wulff
  • Hong Ren
  • Zhensheng Ding
  • Richard J Staples
چکیده

The experimental vibrational circular dichroism, electronic circular dichroism, and optical rotatory dispersion spectra and corresponding quantum chemical predictions of 3,3'-diphenyl-[2,2'-binaphthalene]-1,1'-diol (VANOL) are used to confirm its absolute configuration as (+)(589)-(aR) or (-)(589)-(aS). A discrepancy in the literature crystal structure has been resolved by determining the X-ray crystal structure of the brucine binaphtholphosphate salt of the (aS)-enantiomer of VANOL.

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

منابع مشابه

(R)-1,1′-Binaphthalene-2,2′-diol–(Z)-N-ethyl­ideneethanamine N-oxide (1/1)

In the title compound, C(4)H(9)NO·C(20)H(14)O(2), the dihedral angle between the naphthalene ring systems of the binaphthalene-diol mol-ecule is 77.53 (14)°. In the crystal, the two components are linked by O-H⋯O hydrogen bonds, forming a zigzag chain along the c axis.

متن کامل

2,2′-Bis(meth­oxy­meth­oxy)-3,3′-diphenyl-1,1′-binaphthalene

The asymmetric unit of the title compound, C(36)H(30)O(4), contains two crystallographically independent mol-ecules of similar geometry. In both mol-ecules, the meth-oxy-meth-oxy groups are disordered over two positions with refined site occupancies of 0.613 (3):0.387 (3) and 0.589 (4):0.411 (4). The dihedral angles between the naphthalene planes within the same mol-ecule are 71.72 (7) and 71.7...

متن کامل

A facile synthesis of functionalized 7,8-diaza[5]helicenes through an oxidative ring-closure of 1,1’-binaphthalene-2,2’-diamines (BINAMs)

A facile and moderately functional-group-tolerant synthetic method for the preparation of 7,8-diaza[5]helicenes has been developed. It comprises of an oxidative ring-closing process of 1,1'-binaphthalene-2,2'-diamine (BINAM) derivatives with a chlorine-containing oxidant (t-BuOCl) in the presence of a base (2,6-lutidine). In addition the basic physicochemical properties of newly synthesized com...

متن کامل

2,2′-{[(2,2′-Dieth­oxy-1,1′-binaphthalene-6,6′-di­yl)bis­(4,1-phenyl­ene)]bis­(methan­ylyl­idene)}dimalononitrile

The title compound, C(44)H(30)N(4)O(2), was prepared from 6,6'-dibromo-2,2'-dieth-oxy-1,1'-binaphthalene through a coupling reaction with 4-(4,4,5,5-tetra-methyl-1,3,2-dioxaborolan-2-yl)benzaldehyde followed by a Knoevenagel reaction with malononitrile. The dihedral angle between the symmetry-related naphthalene ring systems is 68.82 (8)° while the dihedral angle between the the naphthalene rin...

متن کامل

Synthesis of bifunctional imido alkylidene bispyrrolide complexes of molybdenum and their conversion into bifunctional imido alkylidene diolate complexes that can be employed as ROMP initiators.

Addition of four equivalents of lithium 2,5-dimethylpyrrolide to a solution of [Mo(NAr)(OR(F6))(2)(CHC(5)H(4))](2)Fe (OR(F6)=OCMe(CF(3))(2)) in dichloromethane led to [Mo(NAr)(Me(2)Pyr)(2)(CHC(5)H(4))](2)Fe (2; Me(2)Pyr=2,5-dimethylpyrrolide) and lithium hexafluoro-tert-butoxide, which crystallizes out upon cooling the reaction mixture to -35 degrees C. Attempts to prepare parent pyrrolide comp...

متن کامل

ذخیره در منابع من


  با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

عنوان ژورنال:
  • The Journal of organic chemistry

دوره 74 15  شماره 

صفحات  -

تاریخ انتشار 2009