Issue 12, 1989

Synthesis of the non-K-region arene oxides and tetrahydro epoxides of dibenz[a,h]anthracene

Abstract

Dibenz[a,h]anthracene 1,2- and 3,4-oxides, (1a) and (2a), as well as the corresponding 1,2,3,4tetrahydro epoxides, (1b) and (2b), were synthesized from 3,4-dihydro- and 1,2-dihydrodibenz[a,h]anthracene, (12) and (17), utilizing bromohydrin ester intermediates. Compounds (12) and (17) were prepared from 3,4-dihydrodibenz[a,h]anthracen-1(2H)-one (10) and 1,2-dihydrodibenz[a,h]anthracen-4(3H)-one (15) in almost quantitative yield. An improved synthesis of (10) is described. 1H N.m.r. analysis revealed that (1a) and (2a) exist at room temperature predominantly as arene oxides and not as oxepines. Spontaneous aromatization of (1a) in aqueous solution at pH 7.4 gave a mixture of the 1- and 2-phenols, while (2a) yielded a mixture of the 3- and 4-phenols.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1989, 2229-2233

Synthesis of the non-K-region arene oxides and tetrahydro epoxides of dibenz[a,h]anthracene

K. L. Platt, H. Frank and F. Oesch, J. Chem. Soc., Perkin Trans. 1, 1989, 2229 DOI: 10.1039/P19890002229

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