Some Phosphorylated Derivatives of Borneol

Cremlyn, Richard J.; Ellam, R. M.; Akhtar, Naseem

doi:10.1080/03086647808069930

Cited by 5 publications

(3 citation statements)

References 5 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…1,2‐Bis(chloroalkoxyphosphanyl)‐1,2‐dicarba‐ closo ‐dodecaboranes(12) 6–8 were prepared from dilithiated ortho ‐carborane and the corresponding dichlorophosphite (R=(‐)‐menthyl, (‐)‐borneyl, adamantyl) in diethyl ether at 0 °C (Scheme ). In the case of 6 , only the ( R P , R P ) isomer ( δ P =161.2 ppm) was obtained by crystallisation in 60 % yield (Figure , Table ).…”

Section: Resultsmentioning

confidence: 99%

Chiral Rhodium(I) Complexes of 1,2‐Bis‐(chloroalkoxyphosphanyl)‐ and 1,2‐Bis‐(amidoalkoxyphosphanyl)‐1,2‐dicarba‐closo‐dodecaboranes(12)

et al. 2017

View full text Add to dashboard Cite

1,2‐Bis(chloroalkoxyphosphanyl)‐1,2‐dicarba‐closo‐dodecaboranes(12) and 1,2‐bis(amido‐(‐)‐menthyloxyphosphanyl)‐1,2‐dicarba‐closo‐dodecaboranes(12) were synthesised by the reaction of dilithiated 1,2‐dicarba‐closo‐dodecaborane(12) with the corresponding dichloro‐ or chloroamidophosphite. For 1,2‐bis‐(chloro‐1‐adamantyloxyphosphanyl)‐1,2‐dicarba‐closo‐dodecaborane(12) epimerisation in solution was observed and the free activation enthalpy was determined experimentally and theoretically. An indirect determination of the meso configuration was obtained by formation of the corresponding molybdenum tetracarbonyl complex. Chlorido‐bridged dimeric chiral rhodium(I) complexes showing planar or folded Rh2Cl2 rings were prepared. Density functional calculations indicate that steric and packing factors play a much more significant role than electronic effects in influencing the bending of the rhodium complexes.

show abstract

Section: Resultsmentioning

confidence: 99%

Chiral Rhodium(I) Complexes of 1,2‐Bis‐(chloroalkoxyphosphanyl)‐ and 1,2‐Bis‐(amidoalkoxyphosphanyl)‐1,2‐dicarba‐closo‐dodecaboranes(12)

et al. 2017

View full text Add to dashboard Cite

show abstract

“…Numerous organophosphorus compounds are well-established pesticides (1). Recently, the synthesis and the reactivity of alicyclic and heterocyclic phosphorochloridates have been studied in some detail with a view to establishing their suitability as potential pesticides (2,(5)(6)(7)(8). In this paper, we present phosphorus-31 NMR data for derivatives of these types of compounds.…”

mentioning

confidence: 99%

“…Chloridates from 1-and 2-adamantols, 1-adamantylamine ( 5), pyrrolidine, morpholine, and piperazine (2) were obtained by a literature method. The various derivatives listed in Tables I-V, viz., amidates, azides, hydrazides, hydrazones, were obtained by treatment of the chloridates with amines, sodium azide, and hydrazine, as previously described (2,5,7,8). Phosphorus NMR spectra were obtained from a Bruker HFX-90 spectrometer operating at 36.43 MHz.…”

mentioning

confidence: 99%

Phosphorus-31 nuclear magnetic resonance data for some compounds containing alicyclic or heterocyclic substituents

Cremlyn¹,

Woods²

1981

J. Chem. Eng. Data

Self Cite

View full text Add to dashboard Cite

show abstract

Planar Chirality from the Chiral Pool: Diastereoselective Anionic Phospho-Fries Rearrangements at Ferrocene

Korb

Lang

2014

Organometallics

View full text Add to dashboard Cite

Exclusively, the anionic phospho-Fries rearrangement has successfully been adopted on chiral ferrocenyl phosphates, resulting in diastereomeric enriched 1,2-P,O-phosphonates (up to 95% de), which can further be converted to an enantiomerically pure phosphane. A simple synthetic protocol for the preparation of all starting materials based on several chiral-pool alcohols, chiral (di)chlorophosphates, and the respective ferrocenyl phosphates is reported. Optimized reaction conditions for the anionic phosphoFries rearrangement allow conversions at ambient temperature and the use of variable lithium amid bases and diamines in hexane, ensure virtually quantitative yields, and avoid side reactions. The (bi)cyclic alkyl substituents result in air-and moisture-stable compounds and furthermore allow the conversion of 1,1′-substituted derivatives to 1,1′,2,2′-functionalized ferrocenes, which is reported for the first time. Simultaneous rearrangements at diferrocenyl phosphates to phosphinates and even 2-hydroxy-1,3-bis(phosphonato) ferrocenes and their workup under ambient conditions can be performed. Single-crystal diffraction analysis allowed the determination of the absolute configuration of the planar chirality of two diastereomerically pure ferrocenes being the R p isomers. Furthermore, strong T-shaped π−π interaction patterns between aromatic C 5 H 3 and C 5 H 4 cycles for three compounds are observed.

show abstract

Some Phosphorylated Derivatives of Borneol

Cited by 5 publications

References 5 publications

Chiral Rhodium(I) Complexes of 1,2‐Bis‐(chloroalkoxyphosphanyl)‐ and 1,2‐Bis‐(amidoalkoxyphosphanyl)‐1,2‐dicarba‐closo‐dodecaboranes(12)

Chiral Rhodium(I) Complexes of 1,2‐Bis‐(chloroalkoxyphosphanyl)‐ and 1,2‐Bis‐(amidoalkoxyphosphanyl)‐1,2‐dicarba‐closo‐dodecaboranes(12)

Phosphorus-31 nuclear magnetic resonance data for some compounds containing alicyclic or heterocyclic substituents

Planar Chirality from the Chiral Pool: Diastereoselective Anionic Phospho-Fries Rearrangements at Ferrocene

Contact Info

Product

Resources

About