Nitration‐Oximization of Styrene Derivatives with <i>tert</i>‐Butyl Nitrite: Synthesis of <i>α</i>‐Nitrooximes

Chumnanvej, Napasawan; Katrun, Praewpan; Pohmakotr, Manat; Reutrakul, Vichai; Soorukram, Darunee; Kuhakarn, Chutima

doi:10.1002/cjoc.201600167

Cited by 9 publications

(7 citation statements)

References 77 publications

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“…We envisaged that the reaction of terminal alkyenes with tertbutyl nitrite was expected to give a similar 2-nitroketone intermediate (Supporting Information, Scheme S1), which was expected to undergo a 1,3-dipolar cycloaddition with the unreacted alkyne, serving as the dienophile. This strategy was tested with different alkynes such as phenylacetylene (19) 24) under the exact experimental conditions to that of styrene (Scheme 2). Interestingly, all the substrates yielded their corresponding isoxazoles (19a), (20a), (21a), (22a), (23a), and (24a) in the range of 34−53% (Scheme 3) rather than isoxazoline derivatives.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

tert-Butyl Nitrite-Mediated Domino Synthesis of Isoxazolines and Isoxazoles from Terminal Aryl Alkenes and Alkynes

Santra

Rakshit

et al. 2017

J. Org. Chem.

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A sequential construction of C-C, C-O, C═N, and C═O bonds from alkenes leading to the direct synthesis of isoxazolines in the presence of tert-butyl nitrite, quinoline, and the Sc(OTf) catalyst in DCE at 80 °C has been accomplished. An unprecedented three consecutive C-H functionalizations of two styrenes are involved in this isoxazoline synthesis. In this radical-mediated reaction, one-half of the aryl alkene is converted into an intermediate 2-nitroketone, which serves as a 1,3-dipolarophile and undergoes cycloaddition with the other half of the unreacted aromatic terminal alkene. The use of an alkyne in lieu of an alkene leads to the formation of isoxazole under identical reaction conditions.

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Section: ■ Results and Discussionmentioning

confidence: 99%

tert-Butyl Nitrite-Mediated Domino Synthesis of Isoxazolines and Isoxazoles from Terminal Aryl Alkenes and Alkynes

Santra

Rakshit

et al. 2017

J. Org. Chem.

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“…In 2015 and 2016, Tan et al . and Kuhakarn et al . independently described the synthesis of α ‐nitrooximes from styrene derivatives with tert ‐butyl nitrite under mild conditions.…”

Section: Methodsmentioning

confidence: 99%

Metal‐Free Regioselective Oxynitration of Acrylamides: Synthesis of 1,2‐Nitro Alcohols

et al. 2019

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A metal-free oxynitration of acrylamides with commercially available tert-butyl nitrite and easily available air was achieved through a regioselective pathway. A wide range of 1,2-nitro alcohols were thus efficiently synthesized in a novel route under mild conditions. The reaction involves a radical process, allows a highly regioselective strategy toward the formation of new CÀ N and CÀ O bonds in one step.

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“…Subsequently, Kuhakarn and co-workers reported a novel method for the synthesis of -nitro ketoximes in good yields using NO/NO 2 radicals with DMSO as the solvent under an air atmosphere at room temperature for 30 minutes (Scheme 3). 15 However, there were some limitations including the use of excess reagent (2 equiv of t-BuONO) and low yields when the substrate contained an electron-releasing substituent.…”

Section: Scheme 2 Synthesis Of -Nitro Ketoximes From Styrenes and T-mentioning

confidence: 99%

Recent Advances in Radical Nitration Using tert-Butyl Nitrite

Song

Dong

et al. 2020

Synthesis

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Nitro compounds serve as valuable intermediates for pharmaceuticals, agrochemicals, dyes, and polymers. In recent years, radical nitration using tert-butyl nitrite (t-BuONO) has attracted wide attention and desirable progress has been made. On the one hand, t-BuONO is a potential active nitro radical source and can react with various functional groups. On the other hand, as a green and novel nitration reagent, t-BuONO has relatively low price and can easily produce a radical under mild conditions, which undoubtedly provides a simple and efficient way for nitration reactions. To date, some important reviews are available that summarize the synthesis of nitro compounds. To the best of our knowledge, however, there is still no review that exclusively discusses the synthesis of nitro compounds using t-BuONO through a radical strategy. Therefore, this review aims to highlight the recent advances in radical nitration using t-BuONO as nitration reagent. The main progress in this area has been presented according to the type of reaction substrates. Special attention has been paid discussion of the reaction mechanisms and selected examples of substrates have been given. We hope this paper will be a useful reference and inspiration for those who are exploring the synthesis of nitro compounds using t-BuONO.1 Introduction2 Radical Nitration of Alkenes3 Radical Nitration of Aromatics4 Radical Nitration of Alkynes5 Radical Nitration of 1,n-Enynes6 Radical Nitration of Alkanes7 Summary and Perspective

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Nitration‐Oximization of Styrene Derivatives with tert‐Butyl Nitrite: Synthesis of α‐Nitrooximes

Cited by 9 publications

References 77 publications

tert-Butyl Nitrite-Mediated Domino Synthesis of Isoxazolines and Isoxazoles from Terminal Aryl Alkenes and Alkynes

tert-Butyl Nitrite-Mediated Domino Synthesis of Isoxazolines and Isoxazoles from Terminal Aryl Alkenes and Alkynes

Metal‐Free Regioselective Oxynitration of Acrylamides: Synthesis of 1,2‐Nitro Alcohols

Recent Advances in Radical Nitration Using tert-Butyl Nitrite

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