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Synthesis 2006(24): 4124-4130  
DOI: 10.1055/s-2006-950371
PAPER
© Georg Thieme Verlag Stuttgart · New York

The Formation of Dialkyl Isobenzofuran-1-ylphosphonates by Lewis Acid Promoted Reaction of o-Phthalaldehyde with Trialkyl Phosphites

Kenji Yamanaa, Toshikazu Ibatab, Hirofumi Nakano*c
a Division of General Science, Aichi Gakuin University, Nisshin, Aichi 470-0195, Japan
b Department of Chemistry, Faculty of Science, Osaka University, Toyonaka, Osaka 560-0043, Japan
c Department of Chemistry, Aichi University of Education, Kariya, Aichi 448-8542, Japan
Fax: +81(566)26 2310; e-Mail: hnakano@auecc.aichi-edu.ac.jp;
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Publication History

Received 27 June 2006
Publication Date:
21 November 2006 (online)

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Abstract

The Lewis acid promoted reaction of o-phthalaldehyde with trialkyl phosphites results in the formation of dialkyl isobenzofuran-1-ylphosphonates, which reacted with various dienophiles, such as N-phenylmaleimide, to give Diels-Alder adducts. The factors influencing the reaction were the strength and amount of the Lewis acid, the solvent, and the alkyl group of the phosphite. Furthermore, the reaction mechanism and rate-determining step were investigated.

Key words

cycloaddition - Diels-Alder reaction - Lewis acids - phosphites - isobenzofuran-1-yl phosphonate