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

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 str...

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Bibliographic Details
Published in:Synthesis (Stuttgart) 2006-12, Vol.2006 (24), p.4124-4130
Main Authors: Yamana, Kenji, Ibata, Toshikazu, Nakano, Hirofumi
Format: Article
Language:English
Online Access:Get full text
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Summary: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.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-2006-950371