KFU. Card publication. Tandem dihetero-Diels–Alder and Huisgen cycloaddition reactions. Synthesis, crystal structure and hydrolysis of the novel cage phosphoranes.

- RUS
- 中文
- ES

TANDEM DIHETERO-DIELS&NDASH;ALDER AND HUISGEN CYCLOADDITION REACTIONS. SYNTHESIS, CRYSTAL STRUCTURE AND HYDROLYSIS OF THE NOVEL CAGE PHOSPHORANES.

Form of presentation

Articles in international journals and collections

Year of publication

2018

��

��

Authors, employees of KFU

Baronova Tamara Aleksandrovna, author

Efimov Sergey Vladimirovich, author

Klochkov Vladimir Vasilevich, author

Mironov Vladimir Fedorovich, author

Mironova Ekaterina Vladimirovna, author

Khasiyatullina Nadezhda Rustemovna, author

Other authors

Litvinov Igor Anatolevich, author

Musin Rashid Zagitovich, author

Fayzullin Robert Rustemovich, author

Bibliographic description in the original language

Tandem dihetero-Diels–Alder and Huisgen cycloaddition reactions. Synthesis, crystal structure and hydrolysis of the novel cage phosphoranes / N.R. Khasiyatullina, T.A. Baronova, E.V. Mironova, R.R. Fayzullin, I.A. Litvinov, S.V. Efimov, R.Z. Musin, V.V. Klochkov and V.F. Mironov // Org. Chem. Front. – 2018. – V. 5, no. 21. – P. 3113–3128. – DOI 10.1039/c8qo00915e

Annotation

The reaction of 2-(1-phenylvinyloxy)benzo-1,3,2-dioxaphosphole with hexafluoroacetone, ethyltrifluoropyruvate and chloral leads to the formation of cage phosphoranes possessing the 1-phospha-2,6,8-trioxabicyclo[3.2.1]octane framework whose structure was established by the XRD method and NMR spectroscopy. The process involves dihetero-Diels–Alder and Huisgen 1,3-dipolar cycloaddition reactions and is accompanied by the simultaneous formation of the P–C and C–C bonds. Despite the generation of three chiral carbon atoms, the stereoselectivity of the process exceeds 96%. Hydrolysis leads to the formation of functionalized aldols and phosphonates.

Keywords

dihetero-Diels?Alder reaction, Huisgen cycloaddition reaction, cage phosphorane, 2-(1-phenylvinyloxy)benzo-1,3,2-dioxaphosphole, hexafluoroacetone, ethyltrifluoropyruvate, chloral, aldol, phosphonate

The name of the journal

Organic Chemistry Frontiers

Please use this ID to quote from or refer to the card

https://repository.kpfu.ru/eng/?p_id=187075&p_lang=2

Full metadata record

Field DC	Value	Language
dc.contributor.author	Baronova Tamara Aleksandrovna	ru_RU
dc.contributor.author	Efimov Sergey Vladimirovich	ru_RU
dc.contributor.author	Klochkov Vladimir Vasilevich	ru_RU
dc.contributor.author	Mironov Vladimir Fedorovich	ru_RU
dc.contributor.author	Mironova Ekaterina Vladimirovna	ru_RU
dc.contributor.author	Khasiyatullina Nadezhda Rustemovna	ru_RU
dc.contributor.author	Litvinov Igor Anatolevich	ru_RU
dc.contributor.author	Musin Rashid Zagitovich	ru_RU
dc.contributor.author	Fayzullin Robert Rustemovich	ru_RU
dc.date.accessioned	2018-01-01T00:00:00Z	ru_RU
dc.date.available	2018-01-01T00:00:00Z	ru_RU
dc.date.issued	2018	ru_RU
dc.identifier.citation	Tandem dihetero-Diels–Alder and Huisgen cycloaddition reactions. Synthesis, crystal structure and hydrolysis of the novel cage phosphoranes / N.R. Khasiyatullina, T.A. Baronova, E.V. Mironova, R.R. Fayzullin, I.A. Litvinov, S.V. Efimov, R.Z. Musin, V.V. Klochkov and V.F. Mironov // Org. Chem. Front. – 2018. – V. 5, no. 21. – P. 3113–3128. – DOI 10.1039/c8qo00915e	ru_RU
dc.identifier.uri	https://repository.kpfu.ru/eng/?p_id=187075&p_lang=2	ru_RU
dc.description.abstract	Organic Chemistry Frontiers	ru_RU
dc.description.abstract	The reaction of 2-(1-phenylvinyloxy)benzo-1,3,2-dioxaphosphole with hexafluoroacetone, ethyltrifluoropyruvate and chloral leads to the formation of cage phosphoranes possessing the 1-phospha-2,6,8-trioxabicyclo[3.2.1]octane framework whose structure was established by the XRD method and NMR spectroscopy. The process involves dihetero-Diels–Alder and Huisgen 1,3-dipolar cycloaddition reactions and is accompanied by the simultaneous formation of the P–C and C–C bonds. Despite the generation of three chiral carbon atoms, the stereoselectivity of the process exceeds 96%. Hydrolysis leads to the formation of functionalized aldols and phosphonates.	ru_RU
dc.language.iso	ru	ru_RU
dc.subject	dihetero-Diels?Alder reaction	ru_RU
dc.subject	Huisgen cycloaddition reaction	ru_RU
dc.subject	cage phosphorane	ru_RU
dc.subject	2-(1-phenylvinyloxy)benzo-1	ru_RU
dc.subject	3	ru_RU
dc.subject	2-dioxaphosphole	ru_RU
dc.subject	hexafluoroacetone	ru_RU
dc.subject	ethyltrifluoropyruvate	ru_RU
dc.subject	chloral	ru_RU
dc.subject	aldol	ru_RU
dc.subject	phosphonate	ru_RU
dc.title	Tandem dihetero-Diels–Alder and Huisgen cycloaddition reactions. Synthesis, crystal structure and hydrolysis of the novel cage phosphoranes.	ru_RU
dc.type	Articles in international journals and collections	ru_RU