Volume 18, Issue 9
Preparative Organic Chemistry
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ChemInform Abstract: Regioselectivity of the Amino-Claisen Rearrangement. The Rearrangements of N-Allyl-9-methoxy-1-oxajulolidinium Bromide and N-Allyl-8-methoxylilolidinium Bromide.

K. KANEKO

K. KANEKO

Coll. Pharm., Niigata, Japan

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H. KATAYAMA

H. KATAYAMA

Coll. Pharm., Niigata, Japan

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Y. SAITO

Y. SAITO

Coll. Pharm., Niigata, Japan

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N. FUJITA

N. FUJITA

Coll. Pharm., Niigata, Japan

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A. KATO

A. KATO

Coll. Pharm., Niigata, Japan

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First published: March 3, 1987

Abstract

Thermolysis of N-allyl-9-methoxy-1-oxajulolidinium bromide (I) and N-allyl-8-methoxylilolidinium bromide (III) gives the meta-rearranged products (IIa) and (IVa) respectively, accompanied by the deallylation products (IIb) and (IVb) respectively.

ChemInform Abstract

Thermolysis of N-allyl-9-methoxy-1-oxajulolidinium bromide (I) and N-allyl-8-methoxylilolidinium bromide (III) gives the meta-rearranged products (IIa) and (IVa) respectively, accompanied by the deallylation products (IIb) and (IVb) respectively. In the presence of sodium hydrogen carbonate para-rearrangement occurs with (III) to give the allyl compounds (V) and (VI) as the main components. NaHCO3has only little effect on the thermolysis of (I), giving (IIa) and (IIb) in 95% and 4% yield respectively. (MS-, IR-, 1H-NMR-data).

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