Issue 4, 1978

Selective reactions using metal phenoxides. Part 2. Reactions with aromatic alcohols

Abstract

The reactions of aryloxymagnesium bromides (1) with aromatic alcohols in benzene have been studied. In most cases when an ortho-OH group is absent in the alcohol, if any reaction occurs at all it is unselective and gives mixtures of ortho- and para-products. High reactivity and ortho-regioselectivity to give 2,2′-dihydroxydi- and tri-phenylmethanes (3) are achieved with the 2-hydroxybenzyl alcohols (2), especially when the OH group is converted into the magnesium salt. The formation of ortho-quinone methides (7) as intermediates has been postulated to account for the high ortho-regioselectivity observed.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1978, 322-325

Selective reactions using metal phenoxides. Part 2. Reactions with aromatic alcohols

G. Casiraghi, G. Casnati, M. Cornia, A. Pochini, G. Sartori and R. Ungaro, J. Chem. Soc., Perkin Trans. 1, 1978, 322 DOI: 10.1039/P19780000322

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