Optical Activity and Absolute Configuration of 2,3 :6,7-Dibenzobicyclo [3.3.1]nona-2,6-diene Derivatives

Abstract

2,3 : 6,7-Dibenzobicyclo[3.3.1]nona-2,6-diene-4,8-diol was synthesized and resolved via (−)-menthoxyacetate. Several kinds of optically active derivatives with the same absolute configuration were prepared from the (−)-diol and their chiroptical properties were recorded. The absolute configuration of this series of compounds was determined to be 1R, 5R by a chemical correlation with (R)-(−)-3-phenylbutanoic acid via (−)-1,3-diphenylglutaric acid and (−)-2,4-diphenylpentane.

The selective mono and difunctionalization of carbocyclic cleft molecules with pyridyl groups and X-ray crystallographic analysis

“…7,10 The dibromobenzoate and diacetate derivatives were synthesized for characterization reasons, the dimenthoxy acetate was synthesized for separation purposes and the cyclic ethers…”

“…Hydrogen atom U iso values were constrained to be 120% of that of the carrier atom except for methyl and hydroxyl-H (150%). The absolute structure for (+)-4b·CH 2 Cl 2 was well determined with absolute structure parameter x = 0.06 (7). Further details are provided in Table 1 …”

“…5 The carbocyclic cleft molecule 2 was initially reported in 1960 by Stetter 6 but was fully characterized and resolved in 1975 by Tatemitsu et al 7 Significant advances in the functionalization of 2 have been developed by the Harding group 8 and an excellent review on its development/ uses has been published ( Figure 1). Of particular interest to our group is the reduced version of 2.…”

Controlling the Assembly of C2-Symmetric Molecular Tectons Using a Thiocarbamate Appended Carbocyclic Cleft Molecule Analogous to Tröger’s Base

“…2 This racemic diol could then be converted to the bis-thiocarbamate by treatment with NaH and excess isothiocyanate. This was accomplished with phenyl, tolyl, 3,5-ditrifluromethylphenyl, methyl, and butyl isothiocyanates giving the desired compounds (±)-10a-e in moderate to good yields.…”

“…The carbocyclic diol cleft molecule 1 [1][2][3] has become a surrogate for Tröger's base (2) in catalysis, 4 supramolecular chemistry [5][6][7] and chiral recognition (figure 1). [8][9][10][11] It is analogous to…”