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.

Free Radical Substitution Reactions of Sulfur Monochloride. A Limited Synthesis of Mercaptans

1973 ◽  
Vol 51 (20) ◽  
pp. 3366-3372 ◽  
Author(s):  
Dennis D. Tanner ◽  
Brian G. Brownlee
Keyword(s):  
Free Radical ◽  
Lithium Aluminum Hydride ◽  
Elemental Sulfur ◽  
Aluminum Hydride ◽  
Lithium Aluminum ◽  
Substitution Reactions ◽  
Sulfur Monochloride ◽  
Hydride Reduction ◽  
Abstraction Reaction ◽  
Radical Substitution

The photolysis of sulfur monochloride with a series of saturated aliphatic hydrocarbons yielded alkyl chlorides, di- and polysulfides, hydrogen chloride, and elemental sulfur. The free radical substitution reactions leading to the production of alkyl chloride and the di- and polysulfides were shown to proceed via a chlorine atom abstraction reaction. The major products, the di- and polysulfides could be transformed quantitatively, by lithium aluminum hydride reduction into their corresponding mercaptans. The reaction describes a simple free radical route to the synthesis of a variety of alkyl mercaptans.

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.

Preparation and Spectral Analysis of 3,3',4,4'-Tetrachloroazobenzene and the Corresponding Azoxy and Hydrazo Analogs

1979 ◽  
Vol 62 (4) ◽  
pp. 746-750
Author(s):  
M T Stephen Hsia ◽  
Charles F Burant
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Chromatographic Method ◽  
Lithium Aluminum Hydride ◽  
Aluminum Hydride ◽  
Lithium Aluminum ◽  
Reverse Phase ◽  
High Pressure Liquid Chromatographic ◽  
Hydride Reduction ◽  
Liquid Chromatographic Method ◽  
Liquid Chromatographic

Abstract An efficient preparation was developed for 3,3',4,4'-tetrachloroazobenzene and the corresponding azoxy and hydrazo derivatives, based on the lithium aluminum hydride reduction of 3,4-dichIoronitrobenzene. Batches were analyzed for purity by using a reverse phase high pressure liquid chromatographic method. All 3 compounds can be synthesized in gram quantities with 97–99% purity. Detailed mass, infrared, and nuclear magnetic resonance spectral analyses are presented.

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