Lithium Aluminum Hydride Reduction of 1-Methyl-cis- and -trans-4-t-Butylcyclohexene Oxide

1965 ◽  
Vol 30 (12) ◽  
pp. 4316-4320 ◽  
Author(s):  
Norman A. LeBel ◽  
G. G. Ecke
Keyword(s):  
Lithium Aluminum Hydride ◽  
Aluminum Hydride ◽  
Lithium Aluminum ◽  
Hydride Reduction ◽  
Cis And Trans

Synthesis oftrans- and cis-α-damascone

1978 ◽  
Vol 56 (10) ◽  
pp. 1368-1371 ◽  
Author(s):  
Hsing-Jang Liu ◽  
Hing-Kwok Hung ◽  
George L. Mhehe ◽  
M. L. Duarte Weinberg
Keyword(s):  
Lithium Aluminum Hydride ◽  
Aluminum Hydride ◽  
Complete Recovery ◽  
Lithium Aluminum ◽  
Magnesium Bromide ◽  
Keto Ester ◽  
Keto Esters ◽  
Hydride Reduction ◽  
Cis And Trans ◽  
Cis Isomer

Se lective thioketalization of a mixture of keto esters 5 and 6 resulted in the exclusive formation of thioketal 7 and complete recovery of keto ester 6. Lithium aluminum hydride reduction of thioketal 7 followed by Moffatt oxidation of the resulting alcohol 8 gave aldehyde 10 which on treatment with a mixture of cis- and trans-1-propenyl magnesium bromide afforded trans- alcohol 11 and its cis isomer 12. Manganese dioxide oxidation of alcohol 11 followed by desulfurization gave trans α-damascone (3). Similarly, alcohol 12 was converted to cis-α-damascone (4).

The Chemistry of Sulfur Curing. IV. Effects of Organic Accelerators on the Reaction of Cyclohexene with Sulfur

1968 ◽  
Vol 41 (5) ◽  
pp. 1339-1347 ◽  
Author(s):  
James R. Wolfe
Keyword(s):  
Lithium Aluminum Hydride ◽  
Aluminum Hydride ◽  
Major Product ◽  
Lithium Aluminum ◽  
Radical Mechanism ◽  
Secondary Products ◽  
Tetramethylthiuram Disulfide ◽  
Hydride Reduction ◽  
Free Radical Mechanism ◽  
Cis And Trans

Abstract Cyclohexene reacts with sulfur at 140° in the presence of zinc dimethyldithio-carbamate, tetramethylthiuram monosulfide, or tetramethylthiuram disulfide, to produce 2-cyclohexene-1-thiol as the major product after lithium aluminum hydride reduction of the polysulfide compounds. Secondary products are cis- and trans-1, 2-eyclohexanedithiol and cyclohexanethiol. Zinc dimethyldithiocarbamate is postulated to promote the reaction via an ionic mechanism as it causes more trans than cis-1, 2-cyclohexanedithiol to be formed. Tetramethylthiuram monosulfide and disulfide are postulated to promote the reaction via a free radical mechanism as they cause more cis- than trans-1, 2-cyclohexanedithiol to be formed.

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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