Attempted Enantioselective Synthesis of Terbutaline. Unexpected Partial Racemization During Lithium Aluminum Hydride Reduction of a Secondary Amide

1995 ◽  
Vol 48 (10) ◽  
pp. 1741 ◽  
Author(s):  
AC Donohue ◽  
WR Jackson
Keyword(s):  
Lithium Aluminum Hydride ◽  
Aluminum Hydride ◽  
Optically Active ◽  
Enantioselective Synthesis ◽  
Lithium Aluminum ◽  
Secondary Amide ◽  
Lithium Aluminium Hydride ◽  
Hydride Reduction ◽  
Lithium Aluminium

Syntheses leading to compounds related to the bronchodilator (–)- terbutaline via optically active cyanohydrins suffered unexpected partial racemization during lithium aluminium hydride reduction of key amide intermediates.

Rearrangements Involving the Tricyclo[3.1.1.03,6]heptyl and Tricyclo[3.2.1.03,6]octyl Systems. Single-Electron Transfer in the Reduction of a Bridgehead Tosylate With Lithium Aluminum Hydride

1992 ◽  
Vol 45 (8) ◽  
pp. 1205 ◽  
Author(s):  
EW Della ◽  
WK Janowski ◽  
PE Pigou
Keyword(s):  
Electron Transfer ◽  
Lithium Aluminum Hydride ◽  
Aluminum Hydride ◽  
Single Electron ◽  
Lithium Aluminum ◽  
Single Electron Transfer ◽  
Lithium Aluminium Hydride ◽  
Alkoxy Radicals ◽  
Lithium Aluminium

The attempted conversion of tricyclo [3.1.1.03,6]heptane-6-methanol (9) into the corresponding tosylate (7) leads instead to a rearranged isomer tricyclo [3.2.1.03,6]oct-6-yl tosylate (10). Treatment of 10 with lithium aluminium hydride affords a mixture of the parent alcohol tricyclo[3.2.1.03,6]octan-6-ol (15) and endo-bicyclo[3.2.l]octan-6-ol. The available evidence suggests that the latter arises by a process which appears to be mediated by alkoxy radicals rather than anions.

ChemInform Abstract: Chiral Lithium Aluminum Hydride Reduction of Ketones

ChemInform ◽  
2010 ◽  
Vol 28 (9) ◽  
pp. no-no
Author(s):  
N. SRIVASTAVA ◽  
A. KUMAR
Keyword(s):  
Lithium Aluminum Hydride ◽  
Aluminum Hydride ◽  
Lithium Aluminum ◽  
Hydride Reduction ◽  
Reduction Of Ketones

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.

Stereochemistry of aziridine formation from ketoximes of bridged ring systems by lithium aluminum hydride reduction on benzobicylo[3.2.1]octenone oximes

Tetrahedron ◽  
1969 ◽  
Vol 25 (2) ◽  
pp. 335-353 ◽  
Author(s):  
K. Kitahonoki ◽  
Y. Takano ◽  
A. Matsuura ◽  
K. Kotera
Keyword(s):  
Lithium Aluminum Hydride ◽  
Aluminum Hydride ◽  
Lithium Aluminum ◽  
Ring Systems ◽  
Hydride Reduction

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.

ChemInform Abstract: AN UNUSUAL LITHIUM ALUMINUM HYDRIDE REDUCTION OF AN ISOLATED OLEFIN IN A 1,2-DIAMINE SYSTEM

1978 ◽  
Vol 9 (27) ◽  
Author(s):  
J. SZMUSZKOVICZ ◽  
J. H. MUSSER ◽  
L. G. LAURIAN
Keyword(s):  
Lithium Aluminum Hydride ◽  
Aluminum Hydride ◽  
Lithium Aluminum ◽  
Hydride Reduction
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