The halonium ion-mediated C-C bond cleavage of cyclohexene-fused isoxazoline N-oxides

Mustafa J. Raihan; Veerababurao Kavala; Qiao Zhi Guan; Chun Wei Kuo; Sunil Kataria; Shifali Shishodia; Donala Janreddy; Pateliya Mujjamil Habib; Ching Fa Yao

doi:10.1002/adsc.201200217

The halonium ion-mediated C-C bond cleavage of cyclohexene-fused isoxazoline N-oxides

Mustafa J. Raihan, Veerababurao Kavala, Qiao Zhi Guan, Chun Wei Kuo, Sunil Kataria, Shifali Shishodia, Donala Janreddy, Pateliya Mujjamil Habib, Ching Fa Yao^*

^*Corresponding author for this work

Department of Chemistry

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

8 Citations (Scopus)

Abstract

A protocol for the N-bromosuccinimide (NBS)- and trichloroisocyanuric acid (TCCA)-mediated cleavage of the C-C bond of isoxazoline N-oxides, fused with a cyclohexene ring, leading to the production of a long-chain diketo-halo-nitrile skeleton is described. The conversion occurs via the formation of a nitric oxide intermediate.

Original language	English
Pages (from-to)	2251-2263
Number of pages	13
Journal	Advanced Synthesis and Catalysis
Volume	354
Issue number	11-12
DOIs	https://doi.org/10.1002/adsc.201200217
Publication status	Published - 2012 Aug 13

Keywords

N-bromosuccinimide (NBS)
isoxazoline N-oxides
nitric oxide
ring cleavage
trichloroisocyanuric acid (TCCA)

ASJC Scopus subject areas

Catalysis
Organic Chemistry

Access to Document

10.1002/adsc.201200217

Cite this

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title = "The halonium ion-mediated C-C bond cleavage of cyclohexene-fused isoxazoline N-oxides",

abstract = "A protocol for the N-bromosuccinimide (NBS)- and trichloroisocyanuric acid (TCCA)-mediated cleavage of the C-C bond of isoxazoline N-oxides, fused with a cyclohexene ring, leading to the production of a long-chain diketo-halo-nitrile skeleton is described. The conversion occurs via the formation of a nitric oxide intermediate.",

keywords = "N-bromosuccinimide (NBS), isoxazoline N-oxides, nitric oxide, ring cleavage, trichloroisocyanuric acid (TCCA)",

author = "Raihan, {Mustafa J.} and Veerababurao Kavala and Guan, {Qiao Zhi} and Kuo, {Chun Wei} and Sunil Kataria and Shifali Shishodia and Donala Janreddy and Habib, {Pateliya Mujjamil} and Yao, {Ching Fa}",

year = "2012",

month = aug,

day = "13",

doi = "10.1002/adsc.201200217",

language = "English",

volume = "354",

pages = "2251--2263",

journal = "Advanced Synthesis and Catalysis",

issn = "1615-4150",

publisher = "Wiley-VCH Verlag",

number = "11-12",

}

TY - JOUR

T1 - The halonium ion-mediated C-C bond cleavage of cyclohexene-fused isoxazoline N-oxides

AU - Raihan, Mustafa J.

AU - Kavala, Veerababurao

AU - Guan, Qiao Zhi

AU - Kuo, Chun Wei

AU - Kataria, Sunil

AU - Shishodia, Shifali

AU - Janreddy, Donala

AU - Habib, Pateliya Mujjamil

AU - Yao, Ching Fa

PY - 2012/8/13

Y1 - 2012/8/13

N2 - A protocol for the N-bromosuccinimide (NBS)- and trichloroisocyanuric acid (TCCA)-mediated cleavage of the C-C bond of isoxazoline N-oxides, fused with a cyclohexene ring, leading to the production of a long-chain diketo-halo-nitrile skeleton is described. The conversion occurs via the formation of a nitric oxide intermediate.

AB - A protocol for the N-bromosuccinimide (NBS)- and trichloroisocyanuric acid (TCCA)-mediated cleavage of the C-C bond of isoxazoline N-oxides, fused with a cyclohexene ring, leading to the production of a long-chain diketo-halo-nitrile skeleton is described. The conversion occurs via the formation of a nitric oxide intermediate.

KW - N-bromosuccinimide (NBS)

KW - isoxazoline N-oxides

KW - nitric oxide

KW - ring cleavage

KW - trichloroisocyanuric acid (TCCA)

UR - http://www.scopus.com/inward/record.url?scp=84864977163&partnerID=8YFLogxK

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U2 - 10.1002/adsc.201200217

DO - 10.1002/adsc.201200217

M3 - Article

AN - SCOPUS:84864977163

SN - 1615-4150

VL - 354

SP - 2251

EP - 2263

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

IS - 11-12

ER -

The halonium ion-mediated C-C bond cleavage of cyclohexene-fused isoxazoline N-oxides

Abstract

Keywords

ASJC Scopus subject areas

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CCDC 844978: Experimental Crystal Structure Determination

Cite this

The halonium ion-mediated C-C bond cleavage of cyclohexene-fused isoxazoline N-oxides

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Datasets

CCDC 844978: Experimental Crystal Structure Determination

Cite this