Dihydro-1,2-diazetes – the preparative chemistry since 1980

Moderhack, Dietrich

doi:10.1007/s10593-019-02412-w

Cited by 6 publications

(2 citation statements)

References 67 publications

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“…Description of the Deazatation Systems. In Scheme 2 we depict all the hypothetical or existing studied compounds that may or may not decompose by a fast pericyclic mechanism with N 2 as leaving group 4,62 (later on we will consider some alternatives to dinitrogen). Some important details of these compounds and reactions:…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Quantum Tunneling Instability in Pericyclic Reactions

Frenklach,

Amlani,

Kozuch

2024

J. Am. Chem. Soc.

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Several cycloreversion reactions of the retro-Diels− Alder type were computationally assessed to understand their quantum tunneling (QT) reactivity. N 2 , CO, and other leaving groups were considered based on their strong exothermicity, as it reduces their thermodynamic and kinetic stabilities. Our results indicate that for many of these reactions, it is essential to take into account their QT decomposition rate, which can massively weaken their molecular stability and shorten their half-lives even at deep cryogenic temperatures. In practical terms, this indicates that many supposedly stable molecules will actually be unsynthesizable or unisolable, and therefore trying to prepare or detect them would be a futile attempt. In addition, we discuss the importance of tunneling to correctly understand the enthalpy of activation and the collective atomic effect on the tunneling kinetic isotope effects to test if third-row atoms can tunnel in a chemical reaction. This project raises the question of the importance of in silico chemistry to guide in vitro chemistry, especially in cases where the latter cannot solve its own uncertainties.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Quantum Tunneling Instability in Pericyclic Reactions

Frenklach,

Amlani,

Kozuch

2024

J. Am. Chem. Soc.

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“…5 Nevertheless, only one report has been published that focuses on the synthesis of tetrazoles from nitrones, and this synthetic approach involved the use of toxic or explosive azide sources, such as hydrogen azide. 6…”

Section: Table 1 Optimization Of the Reaction Condition...mentioning

confidence: 99%

Synthesis of 1,5-Disubstituted Tetrazoles from Nitrones by Using Bis(p-nitrophenyl) Phosphorazidate in the Presence of 4-(Dimethylamino)pyridine

Ishihara¹,

Shioiri²,

Matsugi³

2022

Synlett

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A novel method has been developed for the synthesis of 1,5-disubstituted tetrazoles from nitrones using bis(p-nitrophenyl) phosphorazidate (p-NO2DPPA) in the presence of 4-dimethylaminopyridine. By the mentioned approach, various nitrones were converted to the corresponding tetrazoles. This method enables the preparation of 1,5-disubstituted tetrazoles with no need for stimulative and explosive reagents.

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