Synthesis of β-amino-α-ferrocenyl alcohols

2005 ◽  
Vol 2005 (11) ◽  
pp. 712-715 ◽  
Author(s):  
Hai-Ying Zhao ◽  
Zhan-Xi Bian ◽  
Bao-Guo Li
Keyword(s):  
Lithium Aluminum Hydride ◽  
Aluminum Hydride ◽  
Chain Structure ◽  
Lithium Aluminum ◽  
Polymeric Chain ◽  
X Ray ◽  
H Nmr ◽  
Hydrogen Bonding Interactions ◽  
Trimethylsilyl Ethers ◽  
New Compounds

β-Amino-α-ferrocenyl alcohols [FcC(OH)(R)CH2NH2] (R = Me, Et, nPr, iPr, Ph, p-MeOC6H4, o-ClC6H4, m-ClC6H4, p-ClC6H4, Fc; Fc = C5H4FeC5H5) were prepared by the reduction of cyanohydrin trimethylsilyl ethers of acylferrocenes with lithium aluminum hydride. All new compounds were characterised by elemental analysis, IR and 1H NMR spectroscopies. The X-ray crystal structure of β-amino-α,α-diferrocenylethanol shows that it has a polymeric chain structure with hydrogen bonding interactions between the OH proton and the N of NH2.

Photorearrangement of 2-cyanobicyclo[2.2.1]hept-2-ene. Observation of 1,2- and 1,3-sigmatropic shifts

1982 ◽  
Vol 60 (13) ◽  
pp. 1657-1663 ◽  
Author(s):  
Ikbal A. Akhtar ◽  
John J. McCullough ◽  
Susan Vaitekunas ◽  
Romolo Faggiani ◽  
Colin J. L. Lock
Keyword(s):  
Single Crystals ◽  
Lithium Aluminum Hydride ◽  
Aluminum Hydride ◽  
Major Product ◽  
Molecular Structures ◽  
Lithium Aluminum ◽  
Mercury Vapour ◽  
X Ray ◽  
Crystal And Molecular Structures ◽  
Mercury Vapour Lamp

Irradiation of 2-cyanobicyclo[2.2.1]hept-2-ene (2-cyanonorbornene, 4) in hexane, with the full arc of a mercury vapour lamp, gives the rearrangement products 1-cyanobicyclo[4.1.0]hept-2-ene 5 and 7-cyanotricyclo[4.1.0.03.7]heptane 6 in the ratio 20:1. These products were separated by preparative vpc. The structure of the major product 5 was determined by single crystal X-ray analysis. Reduction of 5 with lithium aluminum hydride gave the corresponding primary amine, which was converted to the p-bromobenzenesulfonamide 9, mp 150–151 °C, which gave single crystals from ethanol–water. The crystal and molecular structures are described. The minor product 6 was hydrogenated to give 7-cyanobicyclo[2.2. 1]heptane. Formation of 5 and 6 may involve concerted σ2s + π2s and σ2a + π2a processes respectively, which are photochemically allowed.

DISILYL ALKANES

1952 ◽  
Vol 30 (9) ◽  
pp. 646-652 ◽  
Author(s):  
W. D. English ◽  
A. Taurins ◽  
R. V. V. Nicholls
Keyword(s):  
Elevated Temperature ◽  
Lithium Aluminum Hydride ◽  
Aluminum Hydride ◽  
Lithium Aluminum ◽  
Physical Constants ◽  
New Compounds

By passing appropriate dichloroalkanes, e.g. 1,1-dichloroethane, over a mixture of silicon and copper at elevated temperature, the new compounds 1,1-bis-trichlorosilylethane, 1,2-bis-trichlorosilylpropane, and 1,4-bis-trichlorosilylbutane and the previously reported bis-trichlorosilylmethane, dichlorosilyltrichlorosilylmethane, and 1,2-bis-trichlorosilylethane were synthesized. Trichloromethane yielded perchlorodisilane; 2-chloropropane gave propene.By causing the chlorosilylalkanes to react with lithium aluminum hydride, disilylmethane, 1,1-disilylethane, 1,2-disilylethane, and 1,2-disilylpropane were synthesized.Several physical constants of the compounds were measured.

Determination of the absolute stereochemistry of the fungal metabolite (R)-(−)-2-(4′-hydroxyphenyl)-2-hydroxyethanoic acid (pisolithin B)

1991 ◽  
Vol 69 (5) ◽  
pp. 772-778 ◽  
Author(s):  
Youla S. Tsantrizos ◽  
Kelvin K. Ogilvie
Keyword(s):  
Absolute Configuration ◽  
Lithium Aluminum Hydride ◽  
Optical Rotation ◽  
Aluminum Hydride ◽  
Lithium Aluminum ◽  
Fungal Metabolite ◽  
H Nmr ◽  
The Absolute ◽  
Absolute Stereochemistry

The antifungal antibiotic pisolithin B (p-hydroxymandelic acid, 2-(4′-hydroxyphenyl)-2-hydroxyethanoic acid, 1a) was shown to have the absolute (R) configuration. The stereochemistry was established via comparison of its optical rotation to that of its synthetic (R) and (S) enantiomers. The synthetic samples were prepared by the stereospecific reduction of the prochiral α-keto acid, p-hydroxybenzoylformic acid (2-(4′-hydroxyphenyl)-2-oxoethanoic acid, 2a), with (R) or (S)-2,2′-dihydroxy-1,1′-binaphthyl lithium aluminum hydride (BINAL-H). The absolute configuration and enantiomeric purity of both products were determined using the 1H NMR of their isobutyl esters in the presence of the chiral solvating agent (R)-(−)-2,2,2-trifluoro-1-(9-anthryl)ethanol. Key words: pisolithin B, p-hydroxymandelic acid, antifungal, absolute configuration.

Development of a hybrid metal-oxides (Li2O-Al2O3-Al3Fe-Al3Fe5O12) reinforced polycaprolactone composite

MRS Advances ◽  
2019 ◽  
Vol 4 (63) ◽  
pp. 3485-3493
Author(s):  
N.N. Zurita-Méndez ◽  
J. Beltran-González ◽  
G. Carbajal-De la Torre ◽  
M.A. Espinosa-Medina
Keyword(s):  
Lithium Aluminum Hydride ◽  
Polymer Network ◽  
Aluminum Hydride ◽  
Lithium Aluminum ◽  
X Ray Diffraction ◽  
X Ray ◽  
Potential Applications ◽  
Nanometric Particles ◽  
Irregular Topography

ABSTRACTThis paper addresses the chemical synthesis and characterization of a composite formed by Li2O-Al2O3-Al3Fe-Al3Fe5O12/PCL which were obtained by the process of reduction of ferric chloride (FeCl3) with lithium aluminum hydride (LiAlH4) in an open atmosphere. The goal of the development of this hybrid material was to perform a superparamagnetic material with several potential applications. The results of the characterizations by scanning electron microscopy (SEM) and vibrating sample magnetometer showed a Li2O-Al2O3-Al3Fe-Al3Fe5O12 “desert rose stone”-like morphology 3D hierarchical powders formation when particles were sintered at 850 °C. Homogeneous nanometric particles after calcination at 1100 °C were observed. X-ray diffraction analysis were performed to determine their composition. Subsequently, the superparamagnetic powders were added by dispersion in a polycaprolactone (PCL) matrix, and then, were evaluated by SEM for the observation of their morphologies. The composite material presented a polymer network with an opened structure, a well dispersion of the oxides particles into the interstices with irregular topography and reliefs.

scholarly journals Spirolucidine, a new Lycopodium alkaloid

1984 ◽  
Vol 62 (2) ◽  
pp. 298-302 ◽  
Author(s):  
William A. Ayer ◽  
Leslie F. Ball ◽  
Lois M. Browne ◽  
Motoo Tori ◽  
Louis T. J. Delbaere ◽  
...  
Keyword(s):  
Spectroscopic Data ◽  
Lithium Aluminum Hydride ◽  
Aluminum Hydride ◽  
Lithium Aluminum ◽  
X Ray ◽  
Hydride Reduction ◽  
Crystallographic Study ◽  
Lycopodium Alkaloid ◽  
Relative Stereochemistry ◽  
New Type

The structure of spirolucidine, a new type of Lycopodium alkaloid related to the lucidines, has been determined. Chemical and spectroscopic data, together with biogenetic considerations, led to the correct constitution of spirolucidine. An X-ray crystallographic study of tetrahydrodeoxyspirolucidine, the lithium aluminum hydride reduction product of spirolucidine, confirmed the constitution and established the relative stereochemistry of the alkaloid.

A total synthesis of (±)-triophamine

1984 ◽  
Vol 62 (1) ◽  
pp. 1-5 ◽  
Author(s):  
Edward Piers ◽  
J. Michael Chong ◽  
Kirk Gustafson ◽  
Raymond J. Andersen
Keyword(s):  
Total Synthesis ◽  
Sulfur Trioxide ◽  
Lithium Aluminum Hydride ◽  
Aluminum Hydride ◽  
Lithium Aluminum ◽  
Yield Reduction ◽  
Diisobutylaluminum Hydride ◽  
H Nmr ◽  
Isomeric Acid ◽  
Nitrophenyl Ester

Treatment of ethyl 2-pentynoate (14) with lithium (phenylthio)(tri-n-butylstannyl)cuprate (12) afforded, in 76% yield, ethyl (Z)-3-(tri-n-butylstannyl)-2-pentenoate (15). On the other hand, when compound 14 was allowed to react with the (tri-n-butylstannyl)copper reagent 13, ethyl (E)-3-(tri-n-butylstannyl)-2-pentenoate (21) was produced in 83% yield. Reduction (diisobutylaluminum hydride, ether) of the esters 15 and 21 gave the alcohols 16 and 22, respectively. Treatment of each of the latter substances with pyridine – sulfur trioxide complex, followed by further reduction of the resultant intermediates with lithium aluminum hydride, provided the geometrically isomeric alkenylstannanes 17 and 23. Conjugate addition of (E)-3-lithio-2-pentene (18) (formed by transmetalation of 17) to compound 19 produced the olefinic trimethylhydrazide 20, which was converted (diisobutylaluminum hydride, ether; pyridinium dichromate, dimethylformamide) into the corresponding carboxylic acid 2. Subjection of compound 23 to a sequence of reactions identical with that used for the conversion of 17 into 2 provided the isomeric acid 3, which was identical (infrared, 1H nmr) with the natural acid derived from triophamine (1). Conversion of 3 into the p-nitrophenyl ester 26, followed by condensation of the latter substance with guanidine, afforded a chromatographically separable mixture of (±)-triophamine (1) and the corresponding diastereomer.

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