<i>o</i>‐Phthalaldehyd aus <i>o</i>‐Phthalsäure‐bis‐dimethylamid mit Lithiumaluminiumhydrid

Weygand, Friedrich; Tietjen, Diedrich

doi:10.1002/cber.19510840712

Cited by 24 publications

(4 citation statements)

References 8 publications

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“…This can probably be taken as one of the causes for the big difference in yields which various authors have reported by their reductions. Neither has the partial reduction of the carbonyl group in amides, with decomposition of the molecule, resulting in the formation of aldehydes (3)(4)(5)(6) or alcohols (1, 7-9), been the subject of systematic research. And finally, no mechanism has yet been proposed which could explain the reduction of amides to amines, or which could formulate the course of the reductive decomposition of amides into aldehydes or alcohols.…”

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confidence: 99%

The Reduction of Acid Amides with Lithium Aluminum Hydride

Mićović¹,

Mihailović²

1953

J. Org. Chem.

315

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This communication is taken in part from the Ph.D. dissertation of M. Lj. Mihailovid. 1190 1. An extensive study on the behavior of acid amides towards lithium aluminum hydride has been carried out and a general preparative procedure has been evolved for the preparation of amines from the corresponding amides. According to this method several mono-and di-substituted amides have been reduced to amines in excellent yields (84-93%).2. Conditions have been studied under which aldehydes and alcohols are obtained by the reduction of amides with lithium aluminum hydride. It was found that N-acylated heterocyclic compounds with aromatic character, namely pyrroles, indoles, and carbazoles, are reduced under normal conditions to alcohols with decomposition of the molecule. By applying special conditions, these compounds gave, by reductive decomposition, aldehydes in good yields. 3. A mechanism has been proposed to explain the course of these reductions.

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The Reduction of Acid Amides with Lithium Aluminum Hydride

Mićović¹,

Mihailović²

1953

J. Org. Chem.

315

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“…It is interesting to compare the reduction of tetraphenylphthalic anhydride and tetraphenylphthalide with similar experiments reported in the literature (7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19). The direct reduction of an anhy dride to a dialcohol is well known.…”

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confidence: 57%

“…The unusual feature of the reduction, of tetraphenylphthalic anhydride is the inability to obtain the diol directly although the intermediate is reduced in good yield under the same conditions to the diol. An explanation is not readily forthcoming although steric factors may play a part (15,16). This work is being continued.…”

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confidence: 95%

“…The direct reduction of an anhy dride to a dialcohol is well known. or an equivalent quantity of lithium aluminum hydride has been reported to give only a mixture of phthalyl alcohol and unreacted phthalic anhydride (16), whereas the inverse addition has given phthalide (19). A dependence upon temperatures has also been noted; namely, that naphthalene-1,2-dicarboxylic acid anhydride gives only the lactone of 2-hydroxymethyl-l-naphthoic acid in ethyl ether (14).…”

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confidence: 99%

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REACTIVITY OF TETRAPHENYL-o-XYLYLENE-α,α'-DIOL AS RELATED TO THAT OF TETRAPHENYLPHTHALIC ANHYDRIDE

Bonner¹,

Finkensieper²,

Becker³

1953

J. Org. Chem.

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The Synthesis of Aldehydes from Carboxylic Acids

Mosettig

2011

Organic Reactions

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The Rosenmund reduction of acid chlorides to the corresponding aldehydes was discussed in volume 4 of this series. There are a number of other less direct methods by which carboxylic acids can be converted into aldehydes and the purpose of this chapter is to consider the more useful of these procedures. Three of these methods, the hydrolytic decomposition of Reissert's compounds, the method of Grundmann, and the reductive desulfurization of thiol esters require acid chlorides as intermediates and in the respect are competitive with the Rosenmund reduction of acid chlorides. In the fourth method method, the McFadyen and Stevens synthesis, acid chlorides may be used for the preparation of the intermediate acyl hydrazides. Two additional methods, (Sonn and Muller, and Stephen) are based on the intermediate imido chlorides. These methods listed appear to be the one ones developed to the point where further discussion is profitable.

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o‐Phthalaldehyd aus o‐Phthalsäure‐bis‐dimethylamid mit Lithiumaluminiumhydrid

Abstract: o‐Phthalsäure‐bis‐dimethylamid oder o‐Phthalsäure‐dipiperidid kann mit LiAlH4 in befriedigender Ausbeute zu o‐Phthalaldehyd reduziert werden.

Cited by 24 publications

References 8 publications

The Reduction of Acid Amides with Lithium Aluminum Hydride

The Reduction of Acid Amides with Lithium Aluminum Hydride

REACTIVITY OF TETRAPHENYL-o-XYLYLENE-α,α'-DIOL AS RELATED TO THAT OF TETRAPHENYLPHTHALIC ANHYDRIDE

The Synthesis of Aldehydes from Carboxylic Acids

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