78. Studies on hydrogen cyanide. Part VII. Aldehydes from aromatic hydrocarbons

Hinkel, Leonard Eric; Ayling, Ernest Edward; Beynon, J. H.

doi:10.1039/jr9360000339

Cited by 18 publications

(11 citation statements)

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“…27 The modified Gattermann ± Koch reaction with the use of the stronger Lewis catalyst SbF 5 instead of BF 3 can lead to diformylation of naphthalene. 28 This reaction afforded a mixture of 1,5-( 9), 1,6- (10), 1,7- (11) and 1,8-diformylnaphthalenes (12) in a total yield of 80% in a ratio of 9 : 10 : 11 : 12 = 51 : 6 : 27 : 16. It should be noted that the positions of substituents in formylation products of naphthalene differ substantially from those in nitration products.…”

Section: Formylation Of Naphthalenes a Naphthalene And Alkylnaphthalenesmentioning

confidence: 99%

“…Gattermann formylation (under the action of a mixture of HCN and HCl in the presence of AlCl 3 , CuCl 2 or other Lewis acids) of naphthalene 12 and a-methylnaphthalene 13 afforded a-naphthaldehyde (2) and its 4-methyl derivative 3. The modification of this reaction consists in replacing HCN by less toxic Zn(CN) 2 (Adams method) 14 or sym-triazine.…”

Section: Formylation Of Naphthalenes a Naphthalene And Alkylnaphthalenesmentioning

confidence: 99%

“…Under the conditions of the Gattermann reaction, 1,6-and 2,6-dimethylnaphthalenes gave aldehydes 4 and 5, respectively. 12 Formylation of 2,3-dimethylnaphthalene should be carried out with thorough control over the reaction temperature. Thus, `normal' product 6 was generated in good yield only at a temperature below 55 8C, whereas it was transformed into 2,4-dimethyl-1-naphthaldehyde (7) at a temperature above 65 8C.…”

Section: Formylation Of Naphthalenes a Naphthalene And Alkylnaphthalenesmentioning

confidence: 99%

“…105 Vinylnaphthalenes 106 and acenaphthylene were also proposed as the starting compounds for the preparation of naphthaldehydes. Ozonolysis of acenaphthylene afforded 1,8diformylnaphthalene (12) in 73% yield. 107 Due, apparently, to Coulombic repulsions between two closely spaced carbonyl groups, this dialdehyde is very readily hydrated and transformed into cyclic hydrate 122 under normal conditions.…”

Section: Oxidation Of Alcohols and Alkylnaphthalenesmentioning

confidence: 99%

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Naphthaldehydes

Пожарский¹

2003

Russ. Chem. Rev.

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Data on methods for the preparation of naphthalde-Data on methods for the preparation of naphthaldehydes, their physicochemical properties, structural characteristics hydes, their physicochemical properties, structural characteristics and reactivities are generalised. Particular attention is given to and reactivities are generalised. Particular attention is given to procedures for formylation of naphthalenes and procedures for formylation of naphthalenes and peri peri-interactions -interactions involving the aldehyde group in the involving the aldehyde group in the a a-position. The bibliography -position. The bibliography includes 201 references includes 201 references. .

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Section: Formylation Of Naphthalenes a Naphthalene And Alkylnaphthalenesmentioning

confidence: 99%

Section: Formylation Of Naphthalenes a Naphthalene And Alkylnaphthalenesmentioning

confidence: 99%

Section: Formylation Of Naphthalenes a Naphthalene And Alkylnaphthalenesmentioning

confidence: 99%

Section: Oxidation Of Alcohols and Alkylnaphthalenesmentioning

confidence: 99%

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Naphthaldehydes

Пожарский¹

2003

Russ. Chem. Rev.

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“…1 that reports the literature dealing with the main topics that compose the present work. 9-Anthraldehyde oxime is a commercially available product that was first synthesized by Hinkel and co-authors [3] in 1935 (m.p. 186-187 °C).…”

Section: Introductionmentioning

confidence: 99%

9-Anthraldehyde oxime: a synthetic tool for variable applications

2020

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Oximes are one of the most important and prolific functional groups in organic chemistry; among them, 9-anthraldehyde oxime represents a valuable example both from the preparative side and the synthetic applications. There are many strategies to prepare 9-anthraldehyde oxime from different functional groups that were summarized in the present review, focusing on the most recent and innovative. The main synthetic applications of 9-anthraldehyde oxime are presented and thoroughly discussed, focusing on the most recent and innovative synthetic strategies. Graphic abstract

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TheGattermann Synthesis of Aldehydes

Truce

2011

Organic Reactions

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Gatterman developed two methods for introducing the aldehdye group into aromatic compounds. The first of these known as the Gatterman Koch reaction uses a mixture of carbon monoxide and hydrogen chloride in the presence of a mixture of anhydrous aluminum chloride and cuprous chloride. It is not adaptable to the preparation of aldehydes from phenols or phenolic ethers, however. The second method employs a mixture of hydrogen cyanide and hydrogen chloride with or without a catalyst and permits the introduction of an aldehdye group into phenols, naphthols, and their ethers under special conditions into aromatic hydrocarbons and related compounds. This chapter is concerned with the second method. The mechanism of the reaction appears to be complex and has not been fully elucidated. Details on the scope, limitations and alternative methods, as well as experimental tests, are detailed.

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78. Studies on hydrogen cyanide. Part VII. Aldehydes from aromatic hydrocarbons

Cited by 18 publications

References 0 publications

Naphthaldehydes

Naphthaldehydes

9-Anthraldehyde oxime: a synthetic tool for variable applications

TheGattermann Synthesis of Aldehydes

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