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

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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 languageEnglish
Pages (from-to)2251-2263
Number of pages13
JournalAdvanced Synthesis and Catalysis
Volume354
Issue number11-12
DOIs
Publication statusPublished - 2012 Aug 13

Keywords

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

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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    Raihan, M. J., Kavala, V., Guan, Q. Z., Kuo, C. W., Kataria, S., Shishodia, S., Janreddy, D., Habib, P. M., & Yao, C. F. (2012). The halonium ion-mediated C-C bond cleavage of cyclohexene-fused isoxazoline N-oxides. Advanced Synthesis and Catalysis, 354(11-12), 2251-2263. https://doi.org/10.1002/adsc.201200217