Selective Regeneration of Carbonyl Compounds from Oximes with N-Bromosuccinimide Under Neutral and Mild Conditions

Bandgar, B. P.; Kale, Ramesh R.; Kunde, Lalita B.

doi:10.1007/pl00010116

Cited by 5 publications

(4 citation statements)

References 8 publications

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“…Bandgar reported a method for the selective regeneration of carbonyl compounds from oximes using NBS under mild conditions. 2066 Reddy also found that oxidative cleavage of oximes can be achieved using NBS in water in the presence of β-cyclodextrin at room temperature to generate the corresponding carbonyl compounds (Scheme 756). 2067 We also found that TsNBr 2 can be used for the oxidative deprotection of oximes to the corresponding carbonyl compounds.…”

Section: Protection and Deprotection Reactionsmentioning

confidence: 99%

“…The conversion of different oximes to the corresponding carbonyl compounds is a well-known reaction. Bandgar reported a method for the selective regeneration of carbonyl compounds from oximes using NBS under mild conditions . Reddy also found that oxidative cleavage of oximes can be achieved using NBS in water in the presence of β-cyclodextrin at room temperature to generate the corresponding carbonyl compounds (Scheme ).…”

Section: Protection and Deprotection Reactionsmentioning

confidence: 99%

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Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

2016

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Bromination is one of the most important transformations in organic synthesis and can be carried out using bromine and many other bromo compounds. Use of molecular bromine in organic synthesis is well-known. However, due to the hazardous nature of bromine, enormous growth has been witnessed in the past several decades for the development of solid bromine carriers. This review outlines the use of bromine and different bromo-organic compounds in organic synthesis. The applications of bromine, a total of 107 bromo-organic compounds, 11 other brominating agents, and a few natural bromine sources were incorporated. The scope of these reagents for various organic transformations such as bromination, cohalogenation, oxidation, cyclization, ring-opening reactions, substitution, rearrangement, hydrolysis, catalysis, etc. has been described briefly to highlight important aspects of the bromo-organic compounds in organic synthesis.

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Section: Protection and Deprotection Reactionsmentioning

confidence: 99%

Section: Protection and Deprotection Reactionsmentioning

confidence: 99%

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

2016

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“…The oxidation of oximes with nitrous acid in solutions is a long known procedure for the recovery of aldehydes and ketones from the parent oximes. , Although the mechanism of the reaction was studied very extensively prior to the 1990s , its stoichiometry is still not well-defined and the nature of intermediates is only partly understood. The recent, growing interest in regeneration of carbonyl compounds from stable and readily prepared oximes – is due to increasing synthetic importance of this method for carbonyls production. It is desirable to develop a method that is environmentally benign and can be applied to a wide range of aldoximes and ketoximes with high selectivity and easy product isolation.…”

Section: Introductionmentioning

confidence: 99%

Photochemistry of Formaldoxime−Nitrous Acid Complexes in an Argon Matrix: Identification of Formaldoxime Nitrite

2009

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We have studied the structure and photochemistry of the formaldoxime−nitrous acid system (CH2NOH−HONO) by help of FTIR matrix isolation spectroscopy and ab initio methods. The MP2/6-311++G(2d,2p) calculations show stability of six isomeric CH2NOH···HONO complexes. The FTIR spectra evidence formation of two hydrogen bonded complexes in an argon matrix whose structures are determined by comparison of the experimental spectra with the calculated ones for the six stable complexes. In the matrix there is present the most stable cyclic complex with two O−H···N bonds; a strong bond is formed between the OH group of HONO and the N atom of CH2NOH and the weaker one between the OH group of CH2NOH and the N atom of HONO. In the other complex present in the matrix the OH group of formaldoxime is attached to the OH group of HONO forming an O−H···O bond. The irradiation of the CH2NOH···HONO complexes with the filtered output of the mercury lamp (λ > 345 nm) leads to the formation of formaldoxime nitrite, CH2NONO, and its two isomeric complexes with water. The main product is the CH2NONO···H2O complex in which water is hydrogen bonded to the N atom of the C═N group. The identity of the photoproducts is confirmed by both FTIR spectroscopy and MP2 or QCISD(full) calculations with the 6-311++G(2d,2p) basis set. The intermediate in this reaction is iminoxyl radical that is formed by abstraction of hydrogen atom from formaldoxime OH group by an OH radical originating from HONO photolysis.

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“…283 Αναγέννηση των μητρικών καρβονυλικών ενώσεων επιτυγχάνεται και με επίδραση Ν-βρωμο-σουκκινιμιδίου (ΝΒS) σε οξίμες, κάτω από ήπιες συνθήκες και σε πολύ καλές αποδόσεις. 284 Επίσης, οι οξίμες σχηματίζουν υδροξυλαμίνες κατά την κατεργασία τους με οργανομαγνησιακές ενώσεις. 285 Με επίδραση υδραζίνης σε αιθανόλη και εφαρμογή θέρμανσης, οι οξίμες μετατρέπονται σε υδραζόνες, σε πολύ καλές αποδόσεις.…”

Section: άλλες αντιδράσειςunclassified

Σύνθεση Αζωτούχων Κουμαρινικών Παραγώγων Και Μελέτη Της Οξείδωσής Τους

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Φασματοσκοπική μελέτη …………………………………………………… 121 11.4 Βιολογική δραστικότητα των Ν-ακυλοϋδραζονών της 7-υδροξυ-8-ακετυλο-κουμαρίνης ………………………………………………………………………… 124 11.4.1 Αντικαρκινική δράση ……………………………………………………….. 124 11.4.2 Αντιοξειδωτική δράση ……………………………………………………… 126 12. ΟΞΕΙΔΩΣΗ ΤΩΝ ΥΔΡΑΖΟΝΩΝ ……………………………………………………… 129 12.1 Οξείδωση των υδραζονών της 7-υδροξυ-8-ακετυλο-κουμαρίνης με τετραοξικό μόλυβδο…………………………………………………………….……………… 129 12.1.1 Ιδιότητες των 7,8-διακυλο κουμαρινών -Φασματοσκοπική μελέτη ……....... 132 12.2 Οξείδωση των Ν-ακυλοϋδραζονών της 6-ακετυλο-7-υδροξυ-κουμαρίνης με τετραοξικό μόλυβδο ………………………………………………………….......... 136 12.2.1 Ιδιότητες των 6,7-διακυλο κουμαρινών -Φασματοσκοπική μελέτη ……… 137 12.3 Οξείδωση των υδραζονών της 7-υδροξυ-8-ακετυλο-κουμαρίνης με διακετοξυιωδοβενζόλιο ………………………………………………………………………. 140

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Selective Regeneration of Carbonyl Compounds from Oximes with N-Bromosuccinimide Under Neutral and Mild Conditions

Abstract: N-Bromosuccinimide has been found to be an ef®cient and selective reagent for the mild oxidative cleavage of oximes to yield their corresponding carbonyl compounds in good to excellent yields.

Cited by 5 publications

References 8 publications

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

Photochemistry of Formaldoxime−Nitrous Acid Complexes in an Argon Matrix: Identification of Formaldoxime Nitrite

Σύνθεση Αζωτούχων Κουμαρινικών Παραγώγων Και Μελέτη Της Οξείδωσής Τους

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