Quinone studies—Istar, open: Evidence for a new type of substitution reaction of phenanthrene-9,10-quinone derivatives

Bhatt, MV (1964) Quinone studies—Istar, open: Evidence for a new type of substitution reaction of phenanthrene-9,10-quinone derivatives. In: Tetrahedron, 20 (4). pp. 803-821.

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Abstract

The para orientation by the carbonyl groups in the bromination of phenanthrenequinone derivatives has been explained on the basis of an excited state resulting from thermal excitation of the quinone and/or from a n→π* transition of the nonbonding electrons of the oxygen atoms. A general preparative method for the syntheses of 3-bromophenanthrenequinone derivatives has been developed. The structure of 2-nitro-6-bromophenanthrenequinone has been established by degradation. Synthesis of 2-nitro-6-bromofluorenone is described. Direct bromination of phenanthrenequinone to 2-bromo and 2,7-dibromo derivatives has also been described.

Item Type:	Journal Article
Publication:	Tetrahedron
Publisher:	Elsevier Science
Additional Information:	Copyright of this article belongs to Elsevier Science.
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	21 May 2010 05:30
Last Modified:	19 Sep 2010 06:07
URI:	http://eprints.iisc.ac.in/id/eprint/27977

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