, volume 18 , issue 8 , pages 1764-1767

Reagents for Storage and Regeneration of Nonstabilized Azomethine Ylides: Spiroanthraceneoxazolidines

Evgeny M Buev ¹

Vladimir S Moshkin ¹

Vyacheslav Ya. Sosnovskikh ¹

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Department of Chemistry, Institute of Natural Sciences, Ural Federal University, 620000 Ekaterinburg, Russian Federation |

Publication type: Journal Article

Publication date: 2016-03-30

American Chemical Society (ACS)

Organic Letters

scimago Q1

wos Q1

SJR: 1.235

CiteScore: 8.7

Impact factor: 5.0

ISSN: 15237060, 15237052

DOI: 10.1021/acs.orglett.6b00475

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PubMed ID: 27028421

Organic Chemistry

Biochemistry

Physical and Theoretical Chemistry

Abstract

Nonstabilized azomethine ylides are easily trapped by anthraquinone to form stable spiro-oxazolidines, which have an unusual ability to undergo a cycloreversion in the presence of other dipolarophiles at 120-150 °C. All tested recycloadditions with carbonyl compounds and electron-poor alkenes occurred in moderate to high yields (41-92%). Moreover, increasing the reaction temperature to 210 °C made it possible to obtain adducts with low reactive dipolarophiles.

Found

15 citations

Sosnovskikh Vyacheslav

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Buev E. M., Moshkin V. S., Sosnovskikh V. Y. Reagents for Storage and Regeneration of Nonstabilized Azomethine Ylides: Spiroanthraceneoxazolidines // Organic Letters. 2016. Vol. 18. No. 8. pp. 1764-1767.

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RIS Copy

TY - JOUR

DO - 10.1021/acs.orglett.6b00475

UR - https://doi.org/10.1021/acs.orglett.6b00475

TI - Reagents for Storage and Regeneration of Nonstabilized Azomethine Ylides: Spiroanthraceneoxazolidines

T2 - Organic Letters

AU - Buev, Evgeny M

AU - Moshkin, Vladimir S

AU - Sosnovskikh, Vyacheslav Ya.

PY - 2016

DA - 2016/03/30

PB - American Chemical Society (ACS)

SP - 1764-1767

IS - 8

VL - 18

PMID - 27028421

SN - 1523-7060

SN - 1523-7052

ER -

BibTex |

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@article{2016_Buev,

author = {Evgeny M Buev and Vladimir S Moshkin and Vyacheslav Ya. Sosnovskikh},

title = {Reagents for Storage and Regeneration of Nonstabilized Azomethine Ylides: Spiroanthraceneoxazolidines},

journal = {Organic Letters},

year = {2016},

volume = {18},

publisher = {American Chemical Society (ACS)},

month = {mar},

url = {https://doi.org/10.1021/acs.orglett.6b00475},

number = {8},

pages = {1764--1767},

doi = {10.1021/acs.orglett.6b00475}

}

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Buev, Evgeny M., et al. “Reagents for Storage and Regeneration of Nonstabilized Azomethine Ylides: Spiroanthraceneoxazolidines.” Organic Letters, vol. 18, no. 8, Mar. 2016, pp. 1764-1767. https://doi.org/10.1021/acs.orglett.6b00475.

Publisher

American Chemical Society (ACS)

Journal

Organic Letters

scimago Q1

wos Q1

SJR

1.235

CiteScore

8.7

Impact factor

5.0

ISSN

15237060 (Print)

15237052 (Electronic)

Labs

Laboratory of Modern Organic Synthesis, INSMa

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