Volume 28, Issue 45
Natural Products
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ChemInform Abstract: Chemical Transformation of 1,8-Cineole. Synthesis of N-Phenylimides from Cineolic Acid.

A. .. J. D. SILVESTRE

A. .. J. D. SILVESTRE

Dep. Chem., Univ. Aveiro, P-3800 Aveiro, Port.

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J. A. S. CAVALEIRO

J. A. S. CAVALEIRO

Dep. Chem., Univ. Aveiro, P-3800 Aveiro, Port.

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A. M. S. SILVA

A. M. S. SILVA

Dep. Chem., Univ. Aveiro, P-3800 Aveiro, Port.

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B. DELMOND

B. DELMOND

Dep. Chem., Univ. Aveiro, P-3800 Aveiro, Port.

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C. FILLIATRE

C. FILLIATRE

Dep. Chem., Univ. Aveiro, P-3800 Aveiro, Port.

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First published: 03 August 2010

Abstract

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ChemInform Abstract

Cineolic acid monophenyl ester (I) is regioselectively converted into the corresponding N-arylimides (IV) in two steps. The regioselectivity of some of the reactions and the heterocyclic ring conformations are established based on spectroscopic data. Imides (IV) are unstable in contact with moisture and undergo regioselective hydrolysis.

chemical structure image

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