23906-87-8Relevant academic research and scientific papers
Optimised synthesis and characterisation of 1-adamantyltrimethylphosphonium iodide
Mansour, Riad,Nejman, Phillip S.,Taylor, Laurence J.,Chalmers, Brian A.,Rey, Fernando,Bengueddach, Abdelkader,Woollins, J. Derek,Slawin, Alexandra M.Z.,Kilian, Petr
, p. 302 - 306 (2017)
A synthetic route to multigram quantities of 1-adamantyltrimethylphosphonium iodide is reported. The synthesis starts from the commercially available precursor 1-adamantyl bromide and was optimised with respect to yield and ease of purification. The title compound is of interest to zeolite chemists as a potent organic structure-directing agent. Full spectroscopic characterisation data of all isolated intermediates and single crystal X-ray diffraction data of AdP(O)Cl2, [AdPMe2H]I and [AdPMe3]I (Ad?=?1-adamantyl) are reported.
Dichlorophosphorylation of adamantanols and 1-adamantylcarbinols in trifluoroacetic acid
Erokhina,Shokova,Luzikov,Kovalev
, p. 851 - 854 (1995)
A convenient method for dichlorophosphorylation of adamantanols and 1-adamantyl alcohols with phosphorus trichloride in trifluoroacetic acid is described. The dichlorophosphoryl group is selectively introduced to the different positions of the adamantane
A Convenient Method for the Synthesis of 1-Adamantyldichlorophosphine
Gouygou, Maryse,Etemad-Moghadam, Guita,Koenig, Max
, p. 508 - 509 (1987)
1-Adamantyldichlorophosphine is obtained in good yield by reduction of 1-adamantyldichlorophosphine sulfide with triphenylphosphine in toluene.It can be quantitatively reduced to 1-adamantylphosphine with lithium alanate in ether.
Defying Stereotypes with Nanodiamonds: Stable Primary Diamondoid Phosphines
Moncea, Oana,Gunawan, Maria A.,Poinsot, Didier,Cattey, Hélène,Becker, Jonathan,Yurchenko, Raisa I.,Butova, Ekaterina D.,Hausmann, Heike,?ekutor, Marina,Fokin, Andrey A.,Hierso, Jean-Cyrille,Schreiner, Peter R.
, p. 8759 - 8769 (2016/10/14)
Direct unequal C-H bond difunctionalization of phosphorylated diamantane was achieved in high yield from the corresponding phosphonates. Reduction of the functionalized phosphonates provides access to novel primary and secondary alkyl/aryl diamantane phos
Recognition characteristics of an adaptive vesicular assembly of amphiphilic baskets for selective detection and mitigation of toxic nerve agents
Chen, Shigui,Ruan, Yian,Brown, Jason D.,Hadad, Christopher M.,Badji, Jovica D.
supporting information, p. 17337 - 17342 (2015/02/02)
We used isothermal titration calorimetry to investigate the affinity of basket 1 (470 ?3) for trapping variously sized and shaped organophosphonates (OPs) 2-12 (137-244 ?3) in water at 298.0 K. The encapsulation is, in each case, dri
Phosphorylation of Adamantane and its Derivatives in Trifluoroacetic Acid Medium
Shokova,Erokhin,Kovalev
, p. 1624 - 1634 (2007/10/03)
The possibility of dichlorophosphorylation of the carcass compounds of the adamantane series and of aryl(alkyl)carbinols, with phosphorus trichloride in the low-nucleophilicity trifluoroacetic acid medium was first demonstrated. A new preparative method for introducing a POCl2 group into the bridgehead and bridge positions of the adamantane nucleus, as well as into the α position of the side chain was developed. Some intermediate adamantyl cations may undergo isometizations, among them skeleton ones. A mechanism of the phosphorylation was proposed.
PHOSPHORYLATED ADAMANTANES. XV. PHOSPHORYLATION OF ADAMANTANE WITH P(III) ACID CHLORIDES IN SULFURIC ACID
Yurchenko, R. I.,Peresypkina, L. P.,Miroshnichenko, V. V.,Yurchenko, A. G.
, p. 1072 - 1076 (2007/10/02)
A new method of introduction of a phosphoryl group into the nodal position of the adamantane nucleus was developed, in which sulfuric acid was used instead of aluminum halides to generate the adamantyl cation in reactions of Br-, OH-, and ONO2-substituted adamantanes and phosphonous and phosphorous chlorides. Relative rates of the hydride shift and skeletal isomerization were qualitatively estimated. Under comparable conditions the rate of the hydride shift in 2-adamantyl carbocation -> 1-adamantyl carbocation is substantially higher than that in the isomerization 1-ethyl-3-adamantyl carbocation -> 1,3-dimethyl-5-adamantyl carbocation.
