Publication

alpha-Hydroxymethylen-verlängerte Aldehyde durch schonende Reduktion von Cyanhydrinen

Manfred Schlosser
1978
Journal Articles

Abstract

The OH group in cyanohydrins RR1C(OH)CN [R = Me2CH, R1 = H; R = R1 = Me; RR1 = (CH2)4, (CH2)5] was protected with EtOCH:CH2 to give RR1C(CN)OCHMeOEt, which were then reduced by NaAlH2(OCH2CH2OMe)2 to RR1C(CHO)OCHMeOEt (I) (53-70%), which were hydrolyzed with dil. acid to RR1C(OH)CHO (these compds. dimerize readily). I reacted with Ph3P+MeBr- and BuLi to give RR1C(CH:CH)OCHMeOEt and with LiAlH4 to give RR1C(CH2OH)OCHMeOEt. Reaction of PhCH(CN)OCHMeOEt with PhMgBr, followed by hydrolysis gave benzoin, and redn. with LiAlH4 in the presence of BzCl gave PhCH(OH)CH2NHBz. [on SciFinder (R)]

Official source

https://infoscience.epfl.ch/entities/publication/5e7b58ba-af7e-4e0b-91e6-91b02ac65e24

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Manfred Schlosser
1978
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/5e7b58ba-af7e-4e0b-91e6-91b02ac65e24

About this result

Related concepts (31)

Lithium aluminium hydride

Lithium aluminium hydride, commonly abbreviated to LAH, is an inorganic compound with the chemical formula or . It is a white solid, discovered by Finholt, Bond and Schlesinger in 1947. This compound is used as a reducing agent in organic synthesis, especially for the reduction of esters, carboxylic acids, and amides. The solid is dangerously reactive toward water, releasing gaseous hydrogen (H2). Some related derivatives have been discussed for hydrogen storage. LAH is a colourless solid but commercial samples are usually gray due to contamination.

Reducing agent

In chemistry, a reducing agent (also known as a reductant, reducer, or electron donor) is a chemical species that "donates" an electron to an (called the , , , or ). Examples of substances that are common reducing agents include the alkali metals, formic acid, oxalic acid, and sulfite compounds. In their pre-reaction states, reducers have extra electrons (that is, they are by themselves reduced) and oxidizers lack electrons (that is, they are by themselves oxidized). This is commonly expressed in terms of their oxidation states.

Group action

In mathematics, a group action on a space is a group homomorphism of a given group into the group of transformations of the space. Similarly, a group action on a mathematical structure is a group homomorphism of a group into the automorphism group of the structure. It is said that the group acts on the space or structure. If a group acts on a structure, it will usually also act on objects built from that structure. For example, the group of Euclidean isometries acts on Euclidean space and also on the figures drawn in it.

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alpha-Hydroxymethylen-verlängerte Aldehyde durch schonende Reduktion von Cyanhydrinen

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