Lithium aluminum hydride reduction of allylic substrates. Notable leaving group effects on the product regiochemistry

1984 ◽  
Vol 49 (21) ◽  
pp. 4084-4086 ◽  
Author(s):  
Tomoatsu Hirabe ◽  
Masatomo Nojima ◽  
Shigekazu Kusabayashi
Keyword(s):  
Lithium Aluminum Hydride ◽  
Aluminum Hydride ◽  
Lithium Aluminum ◽  
Hydride Reduction ◽  
Leaving Group ◽  
Group Effects

The chlorosulfonyl moiety as a leaving group: hydride reduction of sulfonyl chlorides

1979 ◽  
Vol 57 (10) ◽  
pp. 1206-1213 ◽  
Author(s):  
Harvey Owen Fong ◽  
William Rayne Hardstaff ◽  
Denis George Kay ◽  
Richard Francis Langler ◽  
Richard Herman Morse ◽  
...  
Keyword(s):  
Aqueous Phase ◽  
Lithium Aluminum Hydride ◽  
Aluminum Hydride ◽  
Lithium Aluminum ◽  
Two Phase ◽  
Thiol Ester ◽  
Sulfonyl Chlorides ◽  
Hydride Reduction ◽  
Leaving Group

A series of γ-sulfone sulfonyl chlorides undergo a novel reduction upon reaction with lithium aluminum hydride to furnish the corresponding ethyl sulfones. The reactions appear to proceed in an SN2 fashion with the chlorosulfonyl moiety functioning as the leaving group. In general sulfonyl chlorides furnish mercaptans as hydride reduction products.A novel two-phase hydrolysis is shown to convert a thiol ester to a symmetric sulfide which involves hydrolysis and an SN2 displacement in the aqueous phase.

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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