Iron(II)-promoted rearrangement of 1,4-diaryl-2,3-dioxabicyclo[2.2.2]oct-5-enes: A mechanism distinct from that postulated previously

Masaki Kamata; Chika Satoh; Hye Sook Kim; Yusuke Wataya

doi:10.1016/S0040-4039(02)02024-5

Iron(II)-promoted rearrangement of 1,4-diaryl-2,3-dioxabicyclo[2.2.2]oct-5-enes: A mechanism distinct from that postulated previously

Masaki Kamata, Chika Satoh, Hye Sook Kim, Yusuke Wataya

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

16 Citations (Scopus)

Abstract

Reactions of 1,4-diaryl-2,3-dioxabicyclo[2.2.2]oct-5-enes 1a-c (1a: Ar=p-FC₆H₄, 1b: Ar=C₆H₅, 1c: Ar=p-MeC₆H₄) with FeBr₂ afforded syn-1,2;3,4-bis(epoxy)-1,4-diarylcyclohexanes 4a-c and cis-3,6-diaryl-2,3-epoxycyclohexanones 5a-c as major products instead of the previously reported 1-aroyl-3-aryl-2,3-epoxycyclopentanes 2a-c.

Original language	English
Pages (from-to)	8313-8317
Number of pages	5
Journal	Tetrahedron Letters
Volume	43
Issue number	46
DOIs	https://doi.org/10.1016/S0040-4039(02)02024-5
Publication status	Published - Nov 11 2002

Keywords

1,4-diaryl-2,3-dioxabicyclo[2.2.2]oct-5-ene
Antimalarial cyclic peroxide
Bicyclic peroxide
Diepoxide
Epoxyketone
FeBr
Malaria
Mechanism
Rearrangement

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1016/S0040-4039(02)02024-5

Cite this

@article{e07f8f0e3e264d6684f23327b77acf5b,

title = "Iron(II)-promoted rearrangement of 1,4-diaryl-2,3-dioxabicyclo[2.2.2]oct-5-enes: A mechanism distinct from that postulated previously",

abstract = "Reactions of 1,4-diaryl-2,3-dioxabicyclo[2.2.2]oct-5-enes 1a-c (1a: Ar=p-FC6H4, 1b: Ar=C6H5, 1c: Ar=p-MeC6H4) with FeBr2 afforded syn-1,2;3,4-bis(epoxy)-1,4-diarylcyclohexanes 4a-c and cis-3,6-diaryl-2,3-epoxycyclohexanones 5a-c as major products instead of the previously reported 1-aroyl-3-aryl-2,3-epoxycyclopentanes 2a-c.",

keywords = "1,4-diaryl-2,3-dioxabicyclo[2.2.2]oct-5-ene, Antimalarial cyclic peroxide, Bicyclic peroxide, Diepoxide, Epoxyketone, FeBr, Malaria, Mechanism, Rearrangement",

author = "Masaki Kamata and Chika Satoh and Kim, {Hye Sook} and Yusuke Wataya",

year = "2002",

month = nov,

day = "11",

doi = "10.1016/S0040-4039(02)02024-5",

language = "English",

volume = "43",

pages = "8313--8317",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "46",

}

TY - JOUR

T1 - Iron(II)-promoted rearrangement of 1,4-diaryl-2,3-dioxabicyclo[2.2.2]oct-5-enes

T2 - A mechanism distinct from that postulated previously

AU - Kamata, Masaki

AU - Satoh, Chika

AU - Kim, Hye Sook

AU - Wataya, Yusuke

PY - 2002/11/11

Y1 - 2002/11/11

N2 - Reactions of 1,4-diaryl-2,3-dioxabicyclo[2.2.2]oct-5-enes 1a-c (1a: Ar=p-FC6H4, 1b: Ar=C6H5, 1c: Ar=p-MeC6H4) with FeBr2 afforded syn-1,2;3,4-bis(epoxy)-1,4-diarylcyclohexanes 4a-c and cis-3,6-diaryl-2,3-epoxycyclohexanones 5a-c as major products instead of the previously reported 1-aroyl-3-aryl-2,3-epoxycyclopentanes 2a-c.

AB - Reactions of 1,4-diaryl-2,3-dioxabicyclo[2.2.2]oct-5-enes 1a-c (1a: Ar=p-FC6H4, 1b: Ar=C6H5, 1c: Ar=p-MeC6H4) with FeBr2 afforded syn-1,2;3,4-bis(epoxy)-1,4-diarylcyclohexanes 4a-c and cis-3,6-diaryl-2,3-epoxycyclohexanones 5a-c as major products instead of the previously reported 1-aroyl-3-aryl-2,3-epoxycyclopentanes 2a-c.

KW - 1,4-diaryl-2,3-dioxabicyclo[2.2.2]oct-5-ene

KW - Antimalarial cyclic peroxide

KW - Bicyclic peroxide

KW - Diepoxide

KW - Epoxyketone

KW - FeBr

KW - Malaria

KW - Mechanism

KW - Rearrangement

UR - http://www.scopus.com/inward/record.url?scp=0037064483&partnerID=8YFLogxK

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U2 - 10.1016/S0040-4039(02)02024-5

DO - 10.1016/S0040-4039(02)02024-5

M3 - Article

AN - SCOPUS:0037064483

SN - 0040-4039

VL - 43

SP - 8313

EP - 8317

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 46

ER -

Iron(II)-promoted rearrangement of 1,4-diaryl-2,3-dioxabicyclo[2.2.2]oct-5-enes: A mechanism distinct from that postulated previously

Abstract

Keywords

ASJC Scopus subject areas

UN SDGs

Access to Document

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