Issue 3, 1990

1,3-Dipolar cycloadditions to nitrogen-substituted allenes

Abstract

A series of nitrogen-substituted allenes(2ah) was treated with 3,5-dichloro-2,4,6-trimethylbenzonitrile oxide (4) in boiling tetrachloromethane. The reaction occurred predominantly (or exclusively) at the α,β double bond. Regardless of the site of cycloaddition, the carbon of the nitrile oxide bonded selectively to the central carbon of the allene. 4-Methylene-4,5-dihydroisoxazole monoadducts (5) reacted further to form spiro-diadducts. The stereochemistry of one diadduct was determined by X-ray diffraction analysis.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1990, 533-539

1,3-Dipolar cycloadditions to nitrogen-substituted allenes

G. Broggini, L. Bruché, G. Zecchi and T. Pilati, J. Chem. Soc., Perkin Trans. 1, 1990, 533 DOI: 10.1039/P19900000533

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Spotlight

Advertisements