2,5-Dihydro-1,2-oxaphosphol-2-ium Ions, as Highly Reactive Phosphorus-Centered Electrophiles

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2,5-Dihydro-1,2-oxaphosphol-2-ium Ions, as Highly Reactive Phosphorus-Centered Electrophiles : Generation, NMR Study, and Reactions. / Lozovskiy, Stanislav V.; Ivanov, Alexander Yu; Bogachenkov, Alexander S.; Vasilyev, Aleksander V.

In: ChemistrySelect, Vol. 2, No. 16, 31.05.2017, p. 4505-4510.

Research output: Contribution to journal › Article › peer-review

BibTeX

@article{624481b6080246aead0147fff031260a,

title = "2,5-Dihydro-1,2-oxaphosphol-2-ium Ions, as Highly Reactive Phosphorus-Centered Electrophiles: Generation, NMR Study, and Reactions",

abstract = "Diphenyl allenyl phosphonates are cyclized into 2,5-dihydro-1,2-oxaphosphol-2-ium ions in Br{\o}nsted acids (TfOH, H2SO4, FSO3H). These species have been studied by means of 1H, 13C, 31P NMR. The cations react with various nucleophiles (H2O, MeOH, EtOH, Et2NH, PhH) on the phosphorus atom. The obtained products are very labile and undergo decomposition. Contrary to Br{\o}nsted acids, under the action of Lewis acids AlX3 (X=Cl, Br), these diphenyl allenyl phosphonates lead to another kind of heterocycles, 2,5-dihydrobenzo[f][1,2]oxaphosphepine-2-oxides.",

keywords = "1,2-oxaphosphol-2-ium ions, allenes, Br{\o}nsted and Lewis acids, phosphaheterocycles, phosphorus electrophiles",

author = "Lozovskiy, {Stanislav V.} and Ivanov, {Alexander Yu} and Bogachenkov, {Alexander S.} and Vasilyev, {Aleksander V.}",

note = "Publisher Copyright: {\textcopyright} 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2017",

month = may,

day = "31",

doi = "10.1002/slct.201700637",

language = "English",

volume = "2",

pages = "4505--4510",

journal = "ChemistrySelect",

issn = "2365-6549",

publisher = "Wiley-Blackwell",

number = "16",

}

RIS

TY - JOUR

T1 - 2,5-Dihydro-1,2-oxaphosphol-2-ium Ions, as Highly Reactive Phosphorus-Centered Electrophiles

T2 - Generation, NMR Study, and Reactions

AU - Lozovskiy, Stanislav V.

AU - Ivanov, Alexander Yu

AU - Bogachenkov, Alexander S.

AU - Vasilyev, Aleksander V.

PY - 2017/5/31

Y1 - 2017/5/31

N2 - Diphenyl allenyl phosphonates are cyclized into 2,5-dihydro-1,2-oxaphosphol-2-ium ions in Brønsted acids (TfOH, H2SO4, FSO3H). These species have been studied by means of 1H, 13C, 31P NMR. The cations react with various nucleophiles (H2O, MeOH, EtOH, Et2NH, PhH) on the phosphorus atom. The obtained products are very labile and undergo decomposition. Contrary to Brønsted acids, under the action of Lewis acids AlX3 (X=Cl, Br), these diphenyl allenyl phosphonates lead to another kind of heterocycles, 2,5-dihydrobenzo[f][1,2]oxaphosphepine-2-oxides.

AB - Diphenyl allenyl phosphonates are cyclized into 2,5-dihydro-1,2-oxaphosphol-2-ium ions in Brønsted acids (TfOH, H2SO4, FSO3H). These species have been studied by means of 1H, 13C, 31P NMR. The cations react with various nucleophiles (H2O, MeOH, EtOH, Et2NH, PhH) on the phosphorus atom. The obtained products are very labile and undergo decomposition. Contrary to Brønsted acids, under the action of Lewis acids AlX3 (X=Cl, Br), these diphenyl allenyl phosphonates lead to another kind of heterocycles, 2,5-dihydrobenzo[f][1,2]oxaphosphepine-2-oxides.

KW - 1,2-oxaphosphol-2-ium ions

KW - allenes

KW - Brønsted and Lewis acids

KW - phosphaheterocycles

KW - phosphorus electrophiles

UR - http://www.scopus.com/inward/record.url?scp=85028616502&partnerID=8YFLogxK

U2 - 10.1002/slct.201700637

DO - 10.1002/slct.201700637

M3 - Article

AN - SCOPUS:85028616502

VL - 2

SP - 4505

EP - 4510

JO - ChemistrySelect

JF - ChemistrySelect

SN - 2365-6549

IS - 16

ER -

ID: 97790199

2,5-Dihydro-1,2-oxaphosphol-2-ium Ions, as Highly Reactive Phosphorus-Centered Electrophiles: Generation, NMR Study, and Reactions

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