Synlett 2012; 23(10): 1556-1557
DOI: 10.1055/s-0031-1290696
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© Georg Thieme Verlag Stuttgart · New York

2,2,6-Trimethyl-4H-1,3-dioxin-4-one

Mozhdeh Seyyedhamzeh
Department of Chemistry, Shahid Beheshti University, G.C., P.O. Box 19396-4716, Tehran, Iran, Email: [email protected]
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Further Information

Publication History

Publication Date:
29 May 2012 (online)

Dedicated to my research supervisor Prof. Ahmad Shaabani

Introduction

In 1952 Carroll and Bader reported that diketene and acetone can be reacted to afford 2,2,6-trimethyl-4H-1,3-dioxin-4-one (1) (Scheme [1]).[ 1 ]

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Scheme 1

Dioxinone 1 is stable at room temperature, but decom­poses when pyrolyzed into acetylketene 2 and acetone. Therefore, this compound is an important building block in organic synthesis as direct precursor of β-dicarbonyls compounds. Thus, pyrolysis of 1 provides an acetoacetylation procedure in the presence of nucleophiles (Scheme [2]).[ 2 ]

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Scheme 2

Due to the importance of β-dicarbonyls compounds[ 3 ] as excellent materials in the synthesis of heterocyclic compounds, the alternative method for the synthesis of them is the use of acetoacetylating reagents. Because of some drawbacks of using diketene as acetoacetylating reagent, 2,2,6-trimethyl-4H-1,3-dioxin-4-one, a 1:1 acetone diketene adduct is a convenient alternative to diketene.

 
  • References

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