An Unusual Course of the Schmidt Rearrangement in the Reaction of 2H-Azirine-2-carbonyl Azides with Unsaturated Diazoesters.

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An Unusual Course of the Schmidt Rearrangement in the Reaction of 2H-Azirine-2-carbonyl Azides with Unsaturated Diazoesters. / Томашенко, Олеся Александровна ; Конев, Александр Сергеевич ; Хлебников, Александр Феодосиевич.

в: Russian Journal of General Chemistry, Том 92, № 10, 10.2022, стр. 2197-2202.

Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование

BibTeX

@article{45fb907a1b1e49968c0deebfef71bf79,

title = "An Unusual Course of the Schmidt Rearrangement in the Reaction of 2H-Azirine-2-carbonyl Azides with Unsaturated Diazoesters.",

abstract = "Abstract: In the reaction of 2H-azirine-2-carbonyl azides with vinyldiazoacetates at ambient temperatures in the absence of an effective oxidant, a competition takes place between the rearrangement of the azidohydrin intermediate of the Schmidt reaction, leading to pyridine-3-isocyanate, and the decomposition of the intermediate to form deaminated pyridine and cyanic acid. The driving force behind both processes is the elimination of a nitrogen molecule. In the presence of an effective oxidizing agent in the reaction medium, the main process is the Curtius rearrangement of the pyridinecarbonyl azide intermediate, leading to pyridine-3-isocyanate.",

keywords = "2H-azirine-2-carbonyl azides, Curtius rearrangement, Schmidt reaction, pyridines, vinyldiazoacetates",

author = "Томашенко, {Олеся Александровна} and Конев, {Александр Сергеевич} and Хлебников, {Александр Феодосиевич}",

note = "Publisher Copyright: {\textcopyright} 2022, Pleiades Publishing, Ltd.",

year = "2022",

month = oct,

doi = "10.1134/S1070363222100334",

language = "English",

volume = "92",

pages = "2197--2202",

journal = "Russian Journal of General Chemistry",

issn = "1070-3632",

publisher = "МАИК {"}Наука/Интерпериодика{"}",

number = "10",

}

RIS

TY - JOUR

T1 - An Unusual Course of the Schmidt Rearrangement in the Reaction of 2H-Azirine-2-carbonyl Azides with Unsaturated Diazoesters.

AU - Томашенко, Олеся Александровна

AU - Конев, Александр Сергеевич

AU - Хлебников, Александр Феодосиевич

PY - 2022/10

Y1 - 2022/10

N2 - Abstract: In the reaction of 2H-azirine-2-carbonyl azides with vinyldiazoacetates at ambient temperatures in the absence of an effective oxidant, a competition takes place between the rearrangement of the azidohydrin intermediate of the Schmidt reaction, leading to pyridine-3-isocyanate, and the decomposition of the intermediate to form deaminated pyridine and cyanic acid. The driving force behind both processes is the elimination of a nitrogen molecule. In the presence of an effective oxidizing agent in the reaction medium, the main process is the Curtius rearrangement of the pyridinecarbonyl azide intermediate, leading to pyridine-3-isocyanate.

AB - Abstract: In the reaction of 2H-azirine-2-carbonyl azides with vinyldiazoacetates at ambient temperatures in the absence of an effective oxidant, a competition takes place between the rearrangement of the azidohydrin intermediate of the Schmidt reaction, leading to pyridine-3-isocyanate, and the decomposition of the intermediate to form deaminated pyridine and cyanic acid. The driving force behind both processes is the elimination of a nitrogen molecule. In the presence of an effective oxidizing agent in the reaction medium, the main process is the Curtius rearrangement of the pyridinecarbonyl azide intermediate, leading to pyridine-3-isocyanate.

KW - 2H-azirine-2-carbonyl azides

KW - Curtius rearrangement

KW - Schmidt reaction

KW - pyridines

KW - vinyldiazoacetates

UR - http://www.scopus.com/inward/record.url?scp=85141382649&partnerID=8YFLogxK

UR - https://www.mendeley.com/catalogue/5e7eb097-4a11-30ac-99c0-1df940972d45/

U2 - 10.1134/S1070363222100334

DO - 10.1134/S1070363222100334

M3 - Article

VL - 92

SP - 2197

EP - 2202

JO - Russian Journal of General Chemistry

JF - Russian Journal of General Chemistry

SN - 1070-3632

IS - 10

ER -

ID: 100120435