Photoamidation of 3,4,6-Tri-O-acetyl-1,2-dideoxy-D-arabino-hex-1-enopyranose

1972 ◽  
Vol 50 (8) ◽  
pp. 1192-1198 ◽  
Author(s):  
Alex Rosenthal ◽  
A. Zanlungo
Keyword(s):  
Lithium Aluminum Hydride ◽  
Aluminum Hydride ◽  
Acetyl Derivative ◽  
Lithium Aluminum ◽  
Hydride Reduction ◽  
Branched Chain

The acetone-initiated photochemical addition of formamide to 3,4,6-tri-O-acetyl-1,2-dideoxy-D-arabino-hex-1-enopyranose (1) afforded 3,4,6-tri-O-acetyl-2,6-anhydro-3-deoxy-D-gluco-heptonamide (2), 3,4,6-tri-O-acetyl-2,6-anhydro-3-deoxy-D-manno-heptonamide (3), and3,4,6-tri-O-acetyl-1,5-anhydro-2-C-carbamoyl-1,2-dideoxy-D-gluco-hexitol (4) in a combined yield of about 75% (the ratio of yields of 2,3, and 4 was approximately 2:2:3). In addition, trace quantities of the epimeric manno branched-chain adduct of 4, and acetone adducts of 1 were formed. Lithium aluminum hydride reduction of 4 yielded a branched-chain aminopolyol, isolated as its N-acetyl derivative.

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.

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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