Alkene reductions

Phenylcyclopentane [Brpnsted acid catalyzed reduction], alkene to alkane, 125... 

Hydrogen (reduction) alkenes, which are unsaturated compounds, add hydrogen to become saturated compounds ... 

Reductive alkene isomerizations can also be induced by photochemical excitation. Geometric isomerization and rearrangement can be observed upon electron transfer sensitization with molecules with inverse electron demand. Thus, a substituted cinnamyl alcohol in the presence of excited p-dimethoxybenzene gave geometric isomerization and rearrangement characteristic of a free allyl cation, eq. 32 (94) ... 

Alkanes are the most highly reduced of all organic compounds. As a consequence, virtually all preparations of alkanes are reductive. Alkenes and alkynes can both be reduced to alkanes by catalytic hydrogenation. While many catalysts can be employed, palladium on carbon is by far die most common. 

Reduction Alkenes, alkynes, aromatic, aldehydes, ketones, nitriles, carboxylic acids, and carboxylic acid derivatives... 

Baran reported an iron-eatalysed reductive alkene eoupling using phe-nylsilane as the hydrogen source. Using a simple proeedure, both inter-molecular reductive alkene coupling and intramolecular reductive cyclisation were possible. 

Addition compounds called ozonides are produced when alkenes react with ozone and reductive cleavage of these compounds is used extensively in preparative and diagnostic organic chemistry. 

Cobalt has an odd number of electrons, and does not form a simple carbonyl in oxidation state 0. However, carbonyls of formulae Co2(CO)g, Co4(CO)i2 and CoJCO),6 are known reduction of these by an alkali metal dissolved in liquid ammonia (p. 126) gives the ion [Co(CO)4] ". Both Co2(CO)g and [Co(CO)4]" are important as catalysts for organic syntheses. In the so-called oxo reaction, where an alkene reacts with carbon monoxide and hydrogen, under pressure, to give an aldehyde, dicobalt octacarbonyl is used as catalyst ... 

That looks simple and direct don t it If safrole was used as the alkene one would get safrole-azide as product. Just one teensy little reduction away from MDA. Strike also found some azide papers that, with a little work, will get safrole-azide in a totally different way. Strike came across a lot of work where groups were using dinucleophilic addition to get an azide and a halogen added across a double bond. The azide would always go to the beta secondary carbon and the halogen to the primary carbon (just what one would want if safrole was the substrate). 

The addition of N-bromosuccinimide (1.1equiv) to a dichlo-romethane solution containing the alkene (1 equiv) and cyana-mide (4 equiv). The solution was maintained at room temperature (3 days) and then washed with water, dried, and concentrated in vacuo. Treatment of the bromocyanamide [intermediate] with 1% palladium on charcoal in methanol (1h) led to reduction of the for-madine. Addition of base to the reaction mixture (50% aqueous KOH, reflux 6h) followed by extraction with ether gave monoamine. (Yield is 48-64% final amine from alkenes analogous to safrole)... 

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