Caglioti reaction & its Hutchins' modification
Автор: ChemWis
Загружено: 2020-09-18
Просмотров: 997
Описание: In Caglioti reaction, tosylhydrazone of aldehyde or ketone reacts with hydride donors like NaBH4 or LiAlH4 to produce corresponding alkane. Using this reaction we can convert aldehyde group to CH3 and keto group to CH2 just like in the case of Wulf kishner reduction. For example, reduction of tosylhyrazone of cycloheanone in the presensence of sodium borohydride in methanol to cyclohexane and reduction of tosylhydrazone of 1-naphthaldehyde with LiAl4 in dioxane to 1-methylnaphthalene. In Hutchins modification tosyl hydrazones are allowed to react with mild hydride donors like sodiumcyanoborohydrie, In the presence of catalytic amount of acid like p-toluene sulfonic acid in DMF and sulfolane under heating condition to produce alkanes. One thin which is to be noted that , aromatic aldehdes or ketones are not effectively reduced by this method.
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