Issue 4, 1996

Ozone-mediated nitration of naphthalene and some methyl derivatives with nitrogen dioxide. Remarkable enhancement of the 1-nitro/2-nitro isomer ratio and mechanistic implications

Abstract

Naphthalene, 1- and 2-methylnaphthalenes were smoothly nitrated with nitrogen dioxide at low temperatures in the presence of ozone to afford the corresponding vitro derivatives in high yields. For naphthalene, the 1-nitro/2-nitro isomer ratios were remarkably high, mostly ranging from 35 to 70. 1,4-Dimethylnaphthalene suffered extensive side-chain substitution under similar conditions. The enhanced regioselectivity as compared with conventional nitration has been interpreted in terms of the electron transfer mechanism involving the nitrogen trioxide as the initial electrophile.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 2, 1996, 677-683

Ozone-mediated nitration of naphthalene and some methyl derivatives with nitrogen dioxide. Remarkable enhancement of the 1-nitro/2-nitro isomer ratio and mechanistic implications

H. Suzuki and T. Mori, J. Chem. Soc., Perkin Trans. 2, 1996, 677 DOI: 10.1039/P29960000677

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