Configuration of the Diels–Alder Adduct of Hexachlorocyclopentadiene withL-Menthyl Acrylate

Date

1997-7-15

Author

Ülkü, D.
Tahir, M. N.
Demir, A. S.
Akhmedov, I.
Tanyeli, Cihangir

Metadata

Show full item record

Item Usage Stats

183
views

0
downloads

The structure of the title compound, endo-(2R)-(-)-L-menthyl 1,4,5,6,7,7-hexachloro-4-norbornene-2-carboxylate, consists of discrete C18H22CL6O2 molecules related by a twofold screw axis. The relative configuration was determined and the chirality at the unknown centres was assigned on the basis of the known chiral centres of L-menthene. Both the average Csp(2)-Cl, 1.689(5), and Csp(3)-Cl, 1.753(3) Angstrom, distances are a little shorter than the literature values. The six-membered ring of the L-menthyl group has a chair conformation. C-O bond lengths in the carboxylate group are 1.194(7) and 1.323(7) Angstrom.

Subject Keywords

Biological-activity

URI

https://hdl.handle.net/11511/28394

Journal

Acta Crystallographica Section C Crystal Structure Communications

DOI

https://doi.org/10.1107/s0108270197003533

Collections

Department of Chemistry, Article

Suggestions

OpenMETU
Core

Synthesis of Bishomoinositols and an Entry for Construction of a Substituted 3-Oxabicyclo[3.3.1]nonane Skeleton BARAN, ARİF; Bekarlar, Merve; Aydin, Gokay; NEBİOĞLU, MEHMET; ŞAHİN, Ertan; Balcı, Metin (2012-02-03) 1,3,3a,7a-Tetrahydro-2-benzofuran was used as key compound for the synthesis of various bishomoinositol derivatives. The diene was subjected to an epoxidation reaction for further functionalization of the diene unit. The bisepoxide obtained was submitted to a ring-opening reaction with acid in the presence of water. Various bishomoinositols were synthesized. However, when the reaction was carried out in the presence of acetic anhydride, a substituted 3-oxabicyclo[3.3.1]nonane skeleton was formed. The mechan...
Structural and electronic properties of AlP doped Huckel type cyclacene with four benzenoid rings Erkoc, S; Malcıoğlu, Osman Barış (World Scientific Pub Co Pte Lt, 2003-11-01) Cyclacene of the Huckel type having four benzenoid rings have been subjected to centric perturbations along both peripheral circuits such that Al and P atoms are alternatingly located. The present structure of perturbed cyclacene let two types of isomeric compounds to arise such that in one case the peri-positions and fusion-points occupied by Al and P atoms, respectively and in the other case reversal of occupation of locations occur. For these structures, AM1-RHF type semi-empirical calculations have been...
Oxidation of Benzene to Phenol by N2O on an Fe2+-ZSM-5 Cluster: A Density Functional Theory Study Fellah, Mehmet Ferdi; van Santen, Rutger A.; Önal, Işık (2009-08-27) Density functional theory (DFT) calculations were carried out in a study of the oxidation of benzene to phenol by N2O on an Fe2+-ZSM-5 cluster. The catalytic cycle has been studied oil a model [Si6Al2O9H14Fe] cluster. It is found that Fe2+ is preferred over Fe1+ as a site for phenol oxidation. A high desorption value of 126.4 kJ/mol suggests that at low temperature phenol desorption is the rate limiting step on the Fe2+-ZSM-5 cluster. It competes with the N2O decomposition step. The computed activation ener...
Synthesis of heterocyclic amine substituted novel 1,4-Aminoalcohols and applications in various asymmetric transformations Keskin, Eda; Tanyeli, Cihangir; Department of Chemistry (2007) Aminoalcohols are very important compounds used in various asymmetric transformations as chiral ligands or chiral auxiliaries. In this thesis, four novel heterocyclic amine substituted chiral 1,4-aminoalcohols were synthesized. In the synthetic strategy, amide esters were synthesized from (2S, 3R)-3-methoxycarbonylbicyclo[2.2.1]hept-5-ene-2-carboxylic acid by DCC coupling method. Subsequent reduction of these amide esters lead to target 1,4-aminoalcohols. The activities of these novel chiral 1,4-aminoalcoho...
Synthesis of N-substituted Pyrido[4,3-d]pyrimidines for the Large-Scale Production of Self-Assembled Rosettes and Nanotubes DURMUS, Asuman; Günbaş, Emrullah Görkem; Farmer, Steven C.; Ohnstead, Marilyn M.; MASCAL, Mark; Legese, Belete; Cho, Jae-Young; Beingessner, Rachel L.; Yamazaki, Takeshi; Fenniri, Hicham (2013-11-15) N-substituted pyrido[4,3-d]pyrimidines are heterocycles which exhibit the asymmetric hydrogen bonding codes of both guanine and cytosine at 60 degrees angles to each other, such that the molecules self-organize unambiguously into a cyclic hexamer, assembled via 18 intermolecular hydrogen bonds. The synthesis is straightforward and can be concluded in six steps from the commercially available malononitrile dimer. X-ray crystallographic analysis of the supermacrocyclic structure shows an undulating disk with ...

Citation Formats

D. Ülkü, M. N. Tahir, A. S. Demir, I. Akhmedov, and C. Tanyeli, “Configuration of the Diels–Alder Adduct of Hexachlorocyclopentadiene withL-Menthyl Acrylate,” Acta Crystallographica Section C Crystal Structure Communications, pp. 899–901, 1997, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/28394.