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

doi:10.1246/cl.150523

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 journal › Article › peer-review

8 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 language	English
Pages (from-to)	1389-1391
Number of pages	3
Journal	Chemistry Letters
Volume	44
Issue number	10
DOIs	https://doi.org/10.1246/cl.150523
Publication status	Published - 2015
Externally published	Yes

All Science Journal Classification (ASJC) codes

Chemistry(all)

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10.1246/cl.150523

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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.",

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

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volume = "44",

pages = "1389--1391",

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AU - Hirai, Go

AU - Nishizawa, Eri

AU - Kakumoto, Daiki

AU - Morita, Masaki

AU - Okada, Mitsuaki

AU - Hashizume, Daisuke

AU - Nagashima, Sayoko

AU - Sodeoka, Mikiko

PY - 2015

Y1 - 2015

N2 - 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.

AB - 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.

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DO - 10.1246/cl.150523

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JF - Chemistry Letters

IS - 10

ER -

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

Abstract

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