A reactivity study of phenyl and ferrocenyl phosphates within the anionic phospho-Fries rearrangement

Marcus Korb; Heinrich Lang

doi:10.1016/j.inoche.2016.07.017

A reactivity study of phenyl and ferrocenyl phosphates within the anionic phospho-Fries rearrangement

Marcus Korb, Heinrich Lang

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

11 Citations (Scopus)

Abstract

Temperature-dependent anionic phospho-Fries rearrangements of ferrocenyl/phenyl phosphates P(O)(OFc)(n)(OPh)(3) (- n), (Fc = Fe(eta(5)-C5H5)(eta(5)-C5H4); n = 0,1,2,3) were investigated. Whereas ferrocenyls solely undergo one rearrangement per reaction step, the number of phenyl-based 1,3-O -> C shifts depends on the temperature. This results in different types of otherwise hardly accessible mixed ferrocenyl/phenyl organophosphorus compounds. Detailed investigations of the triple-rearrangement of triphenyl phosphate (n = 0) reveals a consecutive formation of its phosphonate and phosphinate prior to the known phosphane oxide. (C) 2016 Elsevier B.V. All rights reserved.

Original language	English
Pages (from-to)	30-32
Number of pages	3
Journal	Inorganic Chemistry Communications
Volume	72
DOIs	https://doi.org/10.1016/j.inoche.2016.07.017
Publication status	Published - 1 Oct 2016
Externally published	Yes

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10.1016/j.inoche.2016.07.017

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title = "A reactivity study of phenyl and ferrocenyl phosphates within the anionic phospho-Fries rearrangement",

abstract = "Temperature-dependent anionic phospho-Fries rearrangements of ferrocenyl/phenyl phosphates P(O)(OFc)(n)(OPh)(3) (- n), (Fc = Fe(eta(5)-C5H5)(eta(5)-C5H4); n = 0,1,2,3) were investigated. Whereas ferrocenyls solely undergo one rearrangement per reaction step, the number of phenyl-based 1,3-O -> C shifts depends on the temperature. This results in different types of otherwise hardly accessible mixed ferrocenyl/phenyl organophosphorus compounds. Detailed investigations of the triple-rearrangement of triphenyl phosphate (n = 0) reveals a consecutive formation of its phosphonate and phosphinate prior to the known phosphane oxide. (C) 2016 Elsevier B.V. All rights reserved.",

keywords = "LIGHT-EMITTING POLYMERS, TRIPHENYLPHOSPHINE OXIDE, EPOXY-RESINS, X-RAY, DERIVATIVES, LIGAND, ACID, LITHIATION, COMPLEX, KETONES",

author = "Marcus Korb and Heinrich Lang",

year = "2016",

month = oct,

day = "1",

doi = "10.1016/j.inoche.2016.07.017",

language = "English",

volume = "72",

pages = "30--32",

journal = "Inorganic Chemistry Communications",

issn = "1387-7003",

publisher = "Pergamon",

}

TY - JOUR

T1 - A reactivity study of phenyl and ferrocenyl phosphates within the anionic phospho-Fries rearrangement

AU - Korb, Marcus

AU - Lang, Heinrich

PY - 2016/10/1

Y1 - 2016/10/1

N2 - Temperature-dependent anionic phospho-Fries rearrangements of ferrocenyl/phenyl phosphates P(O)(OFc)(n)(OPh)(3) (- n), (Fc = Fe(eta(5)-C5H5)(eta(5)-C5H4); n = 0,1,2,3) were investigated. Whereas ferrocenyls solely undergo one rearrangement per reaction step, the number of phenyl-based 1,3-O -> C shifts depends on the temperature. This results in different types of otherwise hardly accessible mixed ferrocenyl/phenyl organophosphorus compounds. Detailed investigations of the triple-rearrangement of triphenyl phosphate (n = 0) reveals a consecutive formation of its phosphonate and phosphinate prior to the known phosphane oxide. (C) 2016 Elsevier B.V. All rights reserved.

AB - Temperature-dependent anionic phospho-Fries rearrangements of ferrocenyl/phenyl phosphates P(O)(OFc)(n)(OPh)(3) (- n), (Fc = Fe(eta(5)-C5H5)(eta(5)-C5H4); n = 0,1,2,3) were investigated. Whereas ferrocenyls solely undergo one rearrangement per reaction step, the number of phenyl-based 1,3-O -> C shifts depends on the temperature. This results in different types of otherwise hardly accessible mixed ferrocenyl/phenyl organophosphorus compounds. Detailed investigations of the triple-rearrangement of triphenyl phosphate (n = 0) reveals a consecutive formation of its phosphonate and phosphinate prior to the known phosphane oxide. (C) 2016 Elsevier B.V. All rights reserved.

KW - LIGHT-EMITTING POLYMERS

KW - TRIPHENYLPHOSPHINE OXIDE

KW - EPOXY-RESINS

KW - X-RAY

KW - DERIVATIVES

KW - LIGAND

KW - ACID

KW - LITHIATION

KW - COMPLEX

KW - KETONES

U2 - 10.1016/j.inoche.2016.07.017

DO - 10.1016/j.inoche.2016.07.017

M3 - Article

VL - 72

SP - 30

EP - 32

JO - Inorganic Chemistry Communications

JF - Inorganic Chemistry Communications

SN - 1387-7003

ER -

A reactivity study of phenyl and ferrocenyl phosphates within the anionic phospho-Fries rearrangement

Abstract

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