<i>TRANS</i>-CYCLOHEXANE-1,2-DIPHOSPHONATES SYNTHESIS, STRUCTURAL AND NMR SPECTROSCOPIC INVESTIGATIONS

Haegele, G.; Peters, Ralf; Kreidler, Kay; Boese, Roland; Großmann, G.; Steglich, F.; Ohms, G.

doi:10.1080/10426509308034350

Cited by 10 publications

(19 citation statements)

References 20 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The remaining hydrogens of the cyclohexane ring occur as a series of multiplets between 1.60 and 0.70 ppm. The expected three resonances are seen in the 13 C{ 1 H} NMR of t-chxnP 2 at 37.6 (t, 1,2 J C-P = 6.4 Hz, PCH) 34.3 (s, PCHCH 2 CH 2 ) and 27.4 ppm (t, 2,3 J C-P = 2.9 Hz, PCHCH 2 CH 2 ). A strong broad peak at 2318 cm −1 in the infrared spectrum of t-chxnP 2 confirms the presence of P-H bonds.…”

Section: Resultsmentioning

confidence: 92%

“…9 Further splitting of the major triplet to afford the observed triplet of triplets arises from 2,3 J P-H couplings to the alpha and beta protons, which coincidentally have the same coupling constant of 21 Hz. A doublet of multiplets centred around 2.75 ppm is seen for the PH hydrogens of the primary phosphines in the 1 H NMR spectrum with the expected 1 J H-P coupling constant of 200 Hz. The remaining hydrogens of the cyclohexane ring occur as a series of multiplets between 1.60 and 0.70 ppm.…”

Section: Resultsmentioning

confidence: 93%

See 1 more Smart Citation

Aspects of the coordination chemistry of rac-trans-1,2-diphosphinocyclohexane and the preparation of reinforced 9aneP₃and 9anePN₂macrocycles

et al. 2014

View full text Add to dashboard Cite

Racemic trans-1,2-diphosphinocyclohexane (t-chxnP2) has been synthesised and its coordination chemistry to Cu(I), Ag(I), Mn(I) and Fe(II) investigated. Compounds of empirical formula [Cu(t-chxnP2)2]BF4 and [Ag(t-chxnP2)2]BF4 have been prepared as isomeric mixtures and the solid-state structure of both complexes determined by single-crystal techniques. The Cu(I) complex is a monomeric species which crystallises with one ligand bearing the R,R configuration and the other being the S,S isomer whereas the Ag(I) complex crystallises as a polymer containing both chelating and bridging t-chxnP2 ligands with 3- and 4-coordinate Ag(I) centres and argentophilic bonds. The bidentate diprimary phosphine has been coordinated to Mn(I) and Fe(II) templates and used as a P2 unit for the formation of chiral (albeit racemic) 1,4,7-triphosphamacrocycles (9aneP3). In addition 1R,2R- and 1R,2S-diaminocyclohexane (chxn) have been coordinated to Mn(I) and Fe(II) templates and similarly employed for the formation of new 1,4-diamino-7-phosphamacrocycle (9anePN2) complexes.

show abstract

Section: Resultsmentioning

confidence: 92%

Section: Resultsmentioning

confidence: 93%

Aspects of the coordination chemistry of rac-trans-1,2-diphosphinocyclohexane and the preparation of reinforced 9aneP₃and 9anePN₂macrocycles

et al. 2014

View full text Add to dashboard Cite

show abstract

“…Scheme 32), Vafina and coworkers [74] observed the addition of trimethyl phosphite to the vinylphosphonate 140, which had been formed by the elimination of nitrous acid from the "expected" P-Michael adduct 139 (Scheme 44). Scheme 44. In order to study the structure of trans-cyclohexanediphosphonic acid (196), Hägele and co-workers [88] performed a P-Michael addition to the unsaturated phosphonate 194. The diphosphonate 195 was obtained in good yield and subsequent acidic hydrolysis led to the desired compound 196 (Scheme 45).…”

Section: Olefinic Acceptors Bearing Phosphonates or Phosphane Oxidesmentioning

confidence: 99%

The Phospha‐Michael Addition in Organic Synthesis

et al. 2005

View full text Add to dashboard Cite

Phosphorus is essential for many reagents in organic synthesis, for ligands of late-transition metals and for phosphonoand phosphanylamino acids, the latter being important isosteres of amino acids. Similar to the Michaelis-Arbuzov and the Michaelis-Becker reaction the phospha-Michael addition, i. e. the addition of a phosphorus nucleophile to an acceptor-substituted alkene or alkyne, certainly represents one of the most versatile and powerful tools for the formation of P-C bonds since many different electrophiles and P nu-

show abstract

“…The pH-dependent rotamer distribution of trans-cyclohexane 1,2-diphosphonic acid has been elucidated [139] using a Karplus equation for 31 P-31 P vicinal coupling constants of α,β-diphosphonates and their esters [140]. Electronegativity-corrected standard trans and gauche values [141] as well as two generalized Karplus-type equations were derived for vicinal 19 F-1 H coupling constants [142,143] that can be used for similar purposes.…”

Section: Miscellaneousmentioning

confidence: 99%

Determination of rotamer populations and related parameters from NMR coupling constants: a critical review

Kraszni

Szakács²,

Noszál³

2004

Analytical and Bioanalytical Chemistry

View full text Add to dashboard Cite

Methods to determine rotamer populations from NMR homo- and heteronuclear vicinal coupling constants are reviewed. Theory and practice related to the elucidation of various gauche and trans limiting coupling constants as key parameters in the characterization of discrete rotational isomers are discussed. Properties and capacities of Karplus-type equations are assessed. Continuous models of rotational isomerism are compared to discrete ones. Principles of the highly specific physicochemical parameters rotamer-specific basicity and rotamer-specific partition coefficient are also described.

show abstract

TRANS-CYCLOHEXANE-1,2-DIPHOSPHONATES SYNTHESIS, STRUCTURAL AND NMR SPECTROSCOPIC INVESTIGATIONS

Cited by 10 publications

References 20 publications

Aspects of the coordination chemistry of rac-trans-1,2-diphosphinocyclohexane and the preparation of reinforced 9aneP₃and 9anePN₂macrocycles

Aspects of the coordination chemistry of rac-trans-1,2-diphosphinocyclohexane and the preparation of reinforced 9aneP₃and 9anePN₂macrocycles

The Phospha‐Michael Addition in Organic Synthesis

Determination of rotamer populations and related parameters from NMR coupling constants: a critical review

Contact Info

Product

Resources

About

TRANS-CYCLOHEXANE-1,2-DIPHOSPHONATES SYNTHESIS, STRUCTURAL AND NMR SPECTROSCOPIC INVESTIGATIONS

Cited by 10 publications

References 20 publications

Aspects of the coordination chemistry of rac-trans-1,2-diphosphinocyclohexane and the preparation of reinforced 9aneP3and 9anePN2macrocycles

Aspects of the coordination chemistry of rac-trans-1,2-diphosphinocyclohexane and the preparation of reinforced 9aneP3and 9anePN2macrocycles

The Phospha‐Michael Addition in Organic Synthesis

Determination of rotamer populations and related parameters from NMR coupling constants: a critical review

Contact Info

Product

Resources

About

Aspects of the coordination chemistry of rac-trans-1,2-diphosphinocyclohexane and the preparation of reinforced 9aneP₃and 9anePN₂macrocycles

Aspects of the coordination chemistry of rac-trans-1,2-diphosphinocyclohexane and the preparation of reinforced 9aneP₃and 9anePN₂macrocycles