Synthese mittlerer und großer Ringe, X. (+)‐ und (−)‐[6]Paracyclophan‐8‐carbonsäure aus (+)‐ und (−)‐3,6‐Hexanooxepin‐4‐carbonsäure

Tochtermann, W.; Vagt, Uwe; Snatzke, Günther

doi:10.1002/cber.19851180523

Cited by 25 publications

(5 citation statements)

References 51 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…A stereospecific synthesis of [6]paracyclophane-8-carboxylic acid (2) was reported, and its CD spectrum was compared with that of [8]paracyclophane-10-carboxylic acid (3, R = CO 2 H) [17]. The former afforded a pair of bisignate CD patterns in the 200-400 nm region, while only a pair of Cotton effect peaks of the same sign were observed for the latter.…”

Section: [N]paracyclophanesmentioning

confidence: 90%

Recent Theoretical and Experimental Advances in the Electronic Circular Dichroisms of Planar Chiral Cyclophanes

Mori

Inoue

2010

Electronic and Magnetic Properties of Chiral Molecules and Supramolecular Architectures

View full text Add to dashboard Cite

The chiroptical properties, such as electronic and vibrational circular dichroism and optical rotation, of planar chiral cyclophanes have attracted much attention in recent years. Although the chemistry of cyclophanes has been extensively explored for more than 60 years, the studies on chiral cyclophanes are rather limited. Experimentally, the use of chiral stationary phases in HPLC becomes more popular and facilitates the enantiomer separation of chiral cyclophanes of interest. Almost all chiral cyclophanes can be readily separated, in analytical and preparative scales, most typically on a Daicel OD type column, which is based on cellulose tris(3,5-dimethylphenylcarbamate). The CD spectra of chiral cyclophanes are unique in their fairly large, significantly coupled Cotton effects observed in all the 1 B b , 1 L a , and 1 L b band regions. Theoretically, the time-dependent density functional theory, or TD-DFT, method becomes a cost-efficient, yet accurate, theoretical method to reproduce the electronic circular dichroisms and the absorption spectra of a variety of cyclophanes. The direct comparison of the experimental CD spectra with the theoretical ones readily leads to the unambiguous assignment of the absolute configuration of cyclophanes. In addition, the analysis of configuration interaction and molecular orbitals allows detailed interpretation of the electronic transitions and Cotton effects in the UV and CD spectra. Through the study of the CD spectra of chiral cyclophanes as model systems, the effects of intra-and intermolecular interactions on the chiroptical properties of molecules can be explored, and the results thus obtained are valuable in comprehensively elucidating the structure-chiroptical property relationship. In this review the recent progress in experimental and theoretical investigations of the electronic CD spectra of chiral cyclophanes is discussed.

show abstract

Section: [N]paracyclophanesmentioning

confidence: 90%

Recent Theoretical and Experimental Advances in the Electronic Circular Dichroisms of Planar Chiral Cyclophanes

Mori

Inoue

2010

Electronic and Magnetic Properties of Chiral Molecules and Supramolecular Architectures

View full text Add to dashboard Cite

show abstract

“…c ( 121.3 (3) 116.4 (3) 115.8 (3) 103.9 (2) 121.6 (3) 130.5 (3) 99.4( 2 ) 115.5(3) 119.0 (3) 101.8(3) ( 23) c (22) 3H, 7'-CH3), 1.08 (s; 3 H,4H,8H,, AB-System bei 5.20 und 5.09 ( J = 12.9 Hz;2H,OCH2),7H,1 5 , (4) 5862 (4) 5849 ( 4) 6886 (4) 6645 (4) 5960 ( 4) 4935 (4) 4252 ( 3 3985(4) 5831 (3) 641 3 ( 3 ) 7512 ( 4) 8220 (3) 7600 (2) 8678 ( 4) 8722 (6) 6303 ( 3) 5887 ( (6) 6758 (5) 8559 (4) 8699 (5) 9356 (5) 9726 (6) 1576 2764 (4) 3422 (4) 3166 (3) 2324 (4) 1635 ( 4) 430 (4) 148 (3) -136 ( 4) -174 (3) 898 (4) 1202 ( ( 10) 1688 (4) 1571 (3) 2269 …”

Section: C( 1 1 )-C( 1 1-c( 12) C(2)-c(3)-c( 4) C(4)-c(5)-c(6) C ( 6)unclassified

Synthese mittlerer und großer Ringe, XIX ¹⁾ Bestimmung der absoluten Konfigurationen von chiralen 3,6‐Hexanooxepinen, [6]Paracyclophanen und verwandten Verbindungen

et al. 1987

Self Cite

View full text Add to dashboard Cite

“…The cyano group, which is known to stabilize radical centres, favours this possibility in the case of 2-cyanobutadiene. The methoxycarbonyl group of 4 should exert a similar effect [12]. In addition, 4 is a butadiene derivative fixed in the s-cis conformation, with C(4)-C(5)-C(6)-C (7) torsion angles of 40.1" (molecule 1 in the asymmetric unit) and 36.2" (molecule 2 in the asymmetric unit) and bond distances C(4)-C(6) and C(5)-C(7) in the range 242-248 pm in the crystalline stateL3I.…”

mentioning

confidence: 97%

Synthesis of Medium and Large Rings, XLIV. Synthesis of Optically Active Bridged Bicyclobutane Derivatives

et al. 1997

Self Cite

View full text Add to dashboard Cite

show abstract

Synthese mittlerer und großer Ringe, X. (+)‐ und (−)‐[6]Paracyclophan‐8‐carbonsäure aus (+)‐ und (−)‐3,6‐Hexanooxepin‐4‐carbonsäure

Cited by 25 publications

References 51 publications

Recent Theoretical and Experimental Advances in the Electronic Circular Dichroisms of Planar Chiral Cyclophanes

Recent Theoretical and Experimental Advances in the Electronic Circular Dichroisms of Planar Chiral Cyclophanes

Synthese mittlerer und großer Ringe, XIX ¹⁾ Bestimmung der absoluten Konfigurationen von chiralen 3,6‐Hexanooxepinen, [6]Paracyclophanen und verwandten Verbindungen

Synthesis of Medium and Large Rings, XLIV. Synthesis of Optically Active Bridged Bicyclobutane Derivatives

Contact Info

Product

Resources

About

Synthese mittlerer und großer Ringe, X. (+)‐ und (−)‐[6]Paracyclophan‐8‐carbonsäure aus (+)‐ und (−)‐3,6‐Hexanooxepin‐4‐carbonsäure

Cited by 25 publications

References 51 publications

Recent Theoretical and Experimental Advances in the Electronic Circular Dichroisms of Planar Chiral Cyclophanes

Recent Theoretical and Experimental Advances in the Electronic Circular Dichroisms of Planar Chiral Cyclophanes

Synthese mittlerer und großer Ringe, XIX 1) Bestimmung der absoluten Konfigurationen von chiralen 3,6‐Hexanooxepinen, [6]Paracyclophanen und verwandten Verbindungen

Synthesis of Medium and Large Rings, XLIV. Synthesis of Optically Active Bridged Bicyclobutane Derivatives

Contact Info

Product

Resources

About

Synthese mittlerer und großer Ringe, XIX ¹⁾ Bestimmung der absoluten Konfigurationen von chiralen 3,6‐Hexanooxepinen, [6]Paracyclophanen und verwandten Verbindungen