The fate of carbonyl-18O in the rearrangement of an acyloxycarbene to a 1,2-dione

Author:

Brown RFC,Browne NR,Eastwood FW

Abstract

5-[carbonyl-18O]Benzoyloxy-2,2,5-trimethyl-1,3-dioxan-4,6-dione (1) was prepared by benzoylation of 5-hydroxy-2,2-dimethyl-1,3-dioxan-4,6-dione with [18O]benzoyl bromide followed by C-methylation.Flash vacuum pyrolysis of(1) at 560�/0.01 mm gave 1-phenyl[1-180]propane-1,2-dione. The position of the label was determined by infrared and mass spectrometry. Scrambling of oxygen to the2-carbonyl group was negligible.

Publisher

CSIRO Publishing

Subject

General Chemistry

Cited by 6 articles. 订阅此论文施引文献 订阅此论文施引文献,注册后可以免费订阅5篇论文的施引文献,订阅后可以查看论文全部施引文献

1. Pyrolysis Involving Compounds with CC, CN and CO Double Bonds;PATAI'S Chemistry of Functional Groups;2009-12-15

2. α,α-Dibromotoluene;Encyclopedia of Reagents for Organic Synthesis;2005-10-15

3. Synthesis and spectra of aldehyde- and ketone-O-(2,5-dihydro-2-methoxy-5,5-dimethyl-1,3,4-oxadiazol-2-yl)oximes — Thermal sources of some methoxy(oximino)carbenes;Canadian Journal of Chemistry;2005-05-01

4. Reactions and Reactivity of Acyloxycarbenes;Journal of the American Chemical Society;1996-01-01

5. Acetoxycarbenes: Modified Oxacarbenes with Enhanced Reactivity;Journal of the American Chemical Society;1994-02

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