Ceric Ammonium Nitrate Oxidation of Carboxylic Acid Hydrazides

Ho, Tse‐Lok; Ho, Honor C.; Wong, C. M.

doi:10.1055/s-1972-21929

Cited by 22 publications

(11 citation statements)

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“…Treatment with ceric salts transforms carboxylic acid hydrazides into the parent acids [46] or their esters [47], substituted hydrazones, semicarbazones, oximes or oxime ethers [48], as well as azines [49] or acetals [50] R…”

Section: Resultsmentioning

confidence: 99%

Synthesis, oxidation and dehydrogenation of cyclic N,O‐ and N,S‐acetals. Part III. Transformation of N,O‐acetals: 3‐acyl‐1,3,4‐oxadiazolines

Somogyi

2007

Journal of Heterocyclic Chem

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Various aldehyde and ketone acylhydrazones are synthesized and, under acylating conditions, cyclized into 3‐acyl‐1,3,4‐oxadiazolines. The scope and limitations of these cyclizations and the possible side reactions (e.g. formation of the open‐chain N,O‐acylhydrazinocarbinols) are dissected. For the first time, simple, convenient and efficient dehydrogenations of 3‐acyl‐1,3,4‐oxadiazolines to oxadiazoles by treatment with potassium permanganate, or more conveniently, with ammonium cerium(IV) nitrate (CAN) are presented. CAN oxidation of 2,2‐disubstituted 3‐acyl‐1,3,4‐oxadiazolines, as well as that of aldehyde diacylhydrazones (open‐chain isomers of 2,5‐disubstituted 3‐acyl‐1,3,4‐oxadiazolines) regenerates the parent carbonyl compounds.

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Section: Resultsmentioning

confidence: 99%

Synthesis, oxidation and dehydrogenation of cyclic N,O‐ and N,S‐acetals. Part III. Transformation of N,O‐acetals: 3‐acyl‐1,3,4‐oxadiazolines

Somogyi

2007

Journal of Heterocyclic Chem

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“…Carboxylic acid hydrazides are oxidized to carboxylic acids by Ce(NH4)2(NO3)6 [71] or Pb(OAc)4 [72] and to aldehydes by K3Fe(CN)6 [73]. Use of uranium hexafluoride also gives carboxylic acids, but reactions proceed slowly, largely owing to the poor solubility of the acid hydrazides in trichlorotrifluoroethane or chloroform.…”

Section: Uf5mentioning

confidence: 99%

Fluorine-Containing Reagents in Organic Synthesis

OLAH

Shih

PRAKASH

2003

World Scientific Series in 20th Century Chemistry

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RCH=CHR' or XZ-AgNO3 ^ (RCHXCHFR) -f RCHFCHFR' (X = Br or I) (60-95%)A simple variation of this procedure affords a-fluoro-(3-nitroalkanes: the alkene is added to a solution of nitronium tetrafluoroborate dissolved in pyridinium poly(hydrogen fluoride), a procedure which eliminates the problem of polymerization usually found in reactions conducted in anhydrous hydrogen fluoride [10], e.g. MeCH=CH2 + [NO21+[BF4]--in PPHF McCHFCH2NO2.Reactions with alcohols [9,11 ] Secondary and tertiary alcohols are readily converted to the corresponding fluorides oy pyridinium poly(hydrogen fluoride). With tertiary Across Conventional Lines Downloaded from www.worldscientific.com by PURDUE UNIVERSITY on 04/13/15. For personal use only.

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“…Therefore, a large number of methods and procedures have been proposed for this type of transformation [6][7][8][9][10][11][12][13][14][15][16][17]. Unfortunately, one or more equivalents of hazardous or toxic oxidizing agents are usually required to achieve this transformation [12][13][14][15][16][17]. Moreover, over-oxidation of sulfoxides to the corresponding sulfones, and also the reaction of other functional groups are common problems in many of the reported methods.…”

Section: Introductionmentioning

confidence: 99%

Selective, metal-free oxidation of sulfides to sulfoxides Using 30% hydrogen peroxide catalyzed with N-bromosuccinimide (NBS) under neutral buffered reaction conditions

Karimi

Zareyee

2008

JICS

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This paper is dedicated to Professor Habib Firouzabadi on the occasion of his 65 th birthday and also his retirement Various types of aromatic and aliphatic sulfides are selectively oxidized to the corresponding sulfoxides in good to excellent yields using 30% H 2 0 2 in the presence of catalytic amounts of N-bromosuccinimide (NBS) in buffered aqueous acetonitrile solution (pH =7.00). The results showed that acid sensitive functional groups such as double bonds, and O,O-acetals remained intact under the described reaction conditions

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Ceric Ammonium Nitrate Oxidation of Carboxylic Acid Hydrazides

Cited by 22 publications

References 0 publications

Synthesis, oxidation and dehydrogenation of cyclic N,O‐ and N,S‐acetals. Part III. Transformation of N,O‐acetals: 3‐acyl‐1,3,4‐oxadiazolines

Synthesis, oxidation and dehydrogenation of cyclic N,O‐ and N,S‐acetals. Part III. Transformation of N,O‐acetals: 3‐acyl‐1,3,4‐oxadiazolines

Fluorine-Containing Reagents in Organic Synthesis

Selective, metal-free oxidation of sulfides to sulfoxides Using 30% hydrogen peroxide catalyzed with N-bromosuccinimide (NBS) under neutral buffered reaction conditions

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