Reactions of carbonyl compounds with phosphorus ylide generated from tribromofluoromethane and tris(dimethylamino)phosphine

Go Hirai, Eri Nishizawa, Daiki Kakumoto, Masaki Morita, Mitsuaki Okada, Daisuke Hashizume, Sayoko Nagashima, Mikiko Sodeoka

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

The reactions of fluorinated ylide, generated from tris(dimethylamino) phosphine and tribromofluoromethane, with simple aldehydes and reactive ketones gave the expected Wittig reaction products. However, a ketone having a galactose skeleton afforded an acid fluoride, probably through an unprecedented CoreyChaykovski- type epoxide formation reaction, followed by spontaneous Meinwald rearrangement.

Original languageEnglish
Pages (from-to)1389-1391
Number of pages3
JournalChemistry Letters
Volume44
Issue number10
DOIs
Publication statusPublished - Jan 1 2015
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

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    Hirai, G., Nishizawa, E., Kakumoto, D., Morita, M., Okada, M., Hashizume, D., Nagashima, S., & Sodeoka, M. (2015). Reactions of carbonyl compounds with phosphorus ylide generated from tribromofluoromethane and tris(dimethylamino)phosphine. Chemistry Letters, 44(10), 1389-1391. https://doi.org/10.1246/cl.150523