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



1974 ◽  
Vol 5 (46) ◽  
pp. no-no
Author(s):  
P. D. HENSON ◽  
S. B. OCKRYMIEK ◽  
R. E. JUN. MARKHAM


1960 ◽  
Vol 38 (9) ◽  
pp. 1434-1438 ◽  
Author(s):  
Gerassimos Frangatos ◽  
Geza Kohan ◽  
Francis L. Chubb

A series of 3-indolylalkylaminoalcohols have been obtained from the lithium aluminum hydride reduction of the amides prepared by the reaction of 3-indoleglyoxylyl chloride and 2-methyl-3-indoleglyoxylyl chloride with primary aminoalcohols. When acetone was used as solvent in the reaction of 3-indoleglyoxylyis chloride and either 2-aminoethanol or 3-aminopropanol, the solvent participated in the reaction resulting in the formation of 2,2-dimethyl-3-(3-indoleglyoxyl)oxazolidine and 2,2-dimethyl-3-(3-indoleglyoxyl)tetrahydro-1,3-oxazine respectively. When the latter two compounds were reduced by lithium aluminum hydride, both carbonyl groups were completely reduced and reductive cleavage of the oxazolidine and tetrahydro-1,3-oxazine rings occurred to form the corresponding open-chain alcohols.





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