Lithium Aluminum Hydride Reactions in Pyridine Solution. IV. Metalation of Di- and Triarylmethanes1

1962 ◽  
Vol 27 (7) ◽  
pp. 2383-2387 ◽  
Author(s):  
Peter T. Lansbury ◽  
Roosevelt Thedford
Keyword(s):  
Lithium Aluminum Hydride ◽  
Aluminum Hydride ◽  
Lithium Aluminum ◽  
Pyridine Solution

A simple synthesis of (±)-1,2,3,6-tetrahydro-2,3′-bipyridine (anatabine) and (±)-3-(2-piperidinyl)pyridine (anabasine) from lithium aluminum hydride and pyridine

1997 ◽  
Vol 75 (6) ◽  
pp. 616-620 ◽  
Author(s):  
Chi-Ming Yang ◽  
Dennis D. Tanner
Keyword(s):  
Catalytic Hydrogenation ◽  
Lithium Aluminum Hydride ◽  
Aluminum Hydride ◽  
Simple Synthesis ◽  
Lithium Aluminum ◽  
Pyridine Solution ◽  
Hydrolysis Of

The hydrolysis of a pyridine solution of lithium tetrakis(N-dihydropyridyl)aluminate (LDPA), which was prepared at 0 °C, yields a mixture of 1,4-, 1,2-, and 2,5-dihydropyridines (DHPs) in a ratio of 26:37:38. The subsequent reversible base-catalyzed condensation of a 1:1 mixture of 1,2- and 2,5-DHPs carried out in the presence of oxygen affords an 89% yield of (±)-anatabine. When the reaction mixture is allowed to stand in the presence of oxygen, anabasine is slowly formed from anatabine by the reaction of the residual DHPs. Anatabine can also be converted into (±)-anabasine by catalytic hydrogenation. Keywords: lithium aluminum hydride, pyridine, anatabine, anabasine.

Lithium Aluminum Hydride Reactions in Pyridine Solution. II. The Role of Steric Effects in the Reductive Cleavage of Pinacolones

1961 ◽  
Vol 26 (7) ◽  
pp. 2277-2280 ◽  
Author(s):  
PETER T. LANSBURY ◽  
JOHN R. ROGOZINSKI ◽  
FAY L. COBLENTZ
Keyword(s):  
Lithium Aluminum Hydride ◽  
Aluminum Hydride ◽  
Reductive Cleavage ◽  
Steric Effects ◽  
Lithium Aluminum ◽  
Pyridine Solution

The Preparation of Specifically Deuterated trans- Cinnamyl Alcohol and trans- Cinnamic Acid

1973 ◽  
Vol 51 (13) ◽  
pp. 2102-2104 ◽  
Author(s):  
Donald G. Lee ◽  
James R. Brownridge
Keyword(s):  
Cinnamic Acid ◽  
Triple Bond ◽  
Lithium Aluminum Hydride ◽  
Aluminum Hydride ◽  
Lithium Aluminum ◽  
Cinnamyl Alcohol ◽  
Partial Reduction ◽  
Work Up

The reduction of ethyl phenylpropiolate by lithium aluminum hydride results in partial reduction of the triple bond to give trans-cinnamyl alcohol. If ethyl phenylpropiolate is reduced by LiAlD4 followed by work-up with acetone and H2O the product is the specifically labeled compound, trans-3-phenyl-2-propen-1-ol-1,1,2-d3. If the ester is reduced with LiAlH4 followed by work-up with acetone-d6 and D2O the product is trans-3-phenyl-2-propen-1-ol-O,3-d2. Oxidation of these two products by sodium ruthenate leads to formation of trans-cinnamic acid-α-d and trans-cinnamic acid-β-d, respectively.

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